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ChemicalBook--->CAS DataBase List--->212650-43-6

212650-43-6

212650-43-6 Structure

212650-43-6 Structure
IdentificationMore
[Name]

MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER
[CAS]

212650-43-6
[Synonyms]

4-N-BOC-3-MORPHOLINECARBOXYLIC ACID
4-(TERT-BUTOXYCARBONYL)MORPHOLINE-3-CARBOXYLIC ACID
MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER
(S)-Morpholine-3,4-dicarboxylic acid 4-tert-butyl
Morpholine-3,4-dicarboxylic acid 4-tert-butyl
N-Boc-Morpholine-2-carboxylic acid
N-Boc-morpholine-3-carboxylic acid
[Molecular Formula]

C10H17NO5
[MDL Number]

MFCD02683057
[Molecular Weight]

231.25
[MOL File]

212650-43-6.mol
Chemical PropertiesBack Directory
[Boiling point ]

369℃
[density ]

1.230
[Fp ]

177℃
[storage temp. ]

2-8°C
[pka]

3.53±0.20(Predicted)
[Appearance]

White to off-white Solid
[InChI]

InChI=1S/C10H17NO5/c1-10(2,3)16-9(14)11-4-5-15-6-7(11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)
[InChIKey]

KVXXEKIGMOEPSA-UHFFFAOYSA-N
[SMILES]

N1(C(OC(C)(C)C)=O)CCOCC1C(O)=O
[CAS DataBase Reference]

212650-43-6(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Sodium hydroxide-->Methanol-->Toluene-->Triethylamine-->Acetone-->Sodium bicarbonate-->Palladium-->Sodium borohydride-->Di-tert-butyl dicarbonate-->Sodium hypochlorite-->Benzaldehyde-->Chloroacetyl chloride-->Potassium bromide-->TEMPO-->DL-Serine-->Sodium bis(2-methoxyethoxy)aluminiumhydride
[Preparation Products]

tert-butyl 3-cyanomorpholine-4-carboxylate
Hazard InformationBack Directory
[Uses]

Morpholine-3,4-dicarboxylic acid 4-tert-butyl ester is an organic heterocyclic compound that can be used in decarboxylation arylation reactions to prepare other compounds. It is also used as a synthetic intermediate component in the preparation of substances such as thienopyrrole compounds, pyridine derivatives and cyclised acetamide derivatives.
[Synthesis]

3-Morpholinecarboxylic acid

77873-76-8

Di-tert-butyl dicarbonate

24424-99-5

MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER

212650-43-6

The general procedure for the synthesis of 4-Boc-3-morpholinecarboxylic acid from 3-morpholinecarboxylic acid and di-tert-butyl dicarbonate is as follows: di-tert-butyl dicarbonate (3.33 g, 15.3 mmol) was slowly added to acetone (5 mL) and water (0 mL) containing morpholine-3-carboxylic acid (1.7 g, 10.2 mmol), potassium carbonate (7.04 g, 51 mmol) in a 0°C in a mixed solution. The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the reaction solution was diluted with water (50 mL) and extracted with ether (2 x 50 mL). The aqueous phase was acidified with 2M aqueous hydrochloric acid (100 mL) and then extracted with dichloromethane (2 x 50 mL). The organic phases were combined, washed sequentially with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the white solid product 4-Boc-3-morpholinecarboxylic acid (1.98 g, 84% yield). The product was characterized by 1H NMR (CDCl3), δ (ppm): 4.46 (m, 2H), 3.80 (m, 3H), 3.53 (m, 1H), 3.31 (m, 1H), 1.48 (d, 9H).

[References]

[1] Patent: WO2005/80386, 2005, A1. Location in patent: Page/Page column 40
[2] Angewandte Chemie - International Edition, 2018,
[3] Angew. Chem., 2018, vol. 130, # 44, p. 14768 - 14773,6
[4] Patent: WO2009/67233, 2009, A1. Location in patent: Page/Page column 46-47
Spectrum DetailBack Directory
[Spectrum Detail]

MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER(212650-43-6)1HNMR
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