Identification | Back Directory | [Name]
3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER | [CAS]
177947-96-5 | [Synonyms]
1-Boc-3-forMylazetidine N-BOC-3-formylazetidine 1-Boc-azetidine-3-carboxa... 1-Boc-3-azetidinecarboxaldehyde 1-Boc-azetidine-3-carboxaldehyde,97% 1-Boc-azetidine-3-carboxaldehyde, 97% ert-butyl3-formylazetidine-1-carboxylate TERT-BUTYL 3-FORMYLAZETIDINE-1-CARBOXYLATE Azetidine-3-carboxaldehyde, N-BOC protected Azetidine-3-carboxaldehyde, N1-BOC protected 1-(tert-Butoxycarbonyl)azetidine-3-carboxaldehyde 1-(tert-Butoxycarbonyl)-3-azetidinecarboxaldehyde Tert butyl 3-formyl azacyclobutane-1-carboxylic acid 3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 1-(tert-Butoxycarbonyl)azetidine-3-carboxaldehyde 1-Azetidinecarboxylic acid, 3-formyl-, 1,1-dimethylethyl ester tert-Butyl 3-formylazetidine-1-carboxylate, N-(tert-Butoxycarbonyl)azetane-3-carboxaldehyde | [EINECS(EC#)]
689-939-0 | [Molecular Formula]
C9H15NO3 | [MDL Number]
MFCD06656142 | [MOL File]
177947-96-5.mol | [Molecular Weight]
185.22 |
Chemical Properties | Back Directory | [Boiling point ]
257℃ | [density ]
1.188 | [refractive index ]
1.4600 to 1.4640 | [Fp ]
109℃ | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [form ]
clear liquid | [pka]
-2.70±0.40(Predicted) | [color ]
Colorless to Light yellow | [Sensitive ]
Air Sensitive | [InChI]
InChI=1S/C9H15NO3/c1-9(2,3)13-8(12)10-4-7(5-10)6-11/h6-7H,4-5H2,1-3H3 | [InChIKey]
JVQOZRRUGOADSU-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CC(C=O)C1 |
Hazard Information | Back Directory | [Uses]
1-Boc-azetidine-3-carboxaldehyde is used as a starting material in organic synthesis. It is also used as an intermediate in pharmaceuticals. | [Synthesis]
The general procedure for the synthesis of tert-butyl 3-formylazetidine-1-carboxylate from 1-Boc-3-hydroxymethylazetidine was as follows: to a stirred solution of oxalyl chloride (4.28 mL, 49.8 mmol) in dichloromethane (DCM, 5 mL) was added slowly and dropwise to dimethylsulfoxide (DMSO, 0.71 mL, 9.96 mmol) at -78 °C. The reaction mixture was continued to be stirred at this temperature for 15 minutes. Subsequently, tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (0.69 g, 3.69 mmol) was added and triethylamine (2.1 mL, 14.75 mmol) was added immediately. The reaction system was gradually warmed to room temperature and diluted with DCM (30 mL). The reaction solution was washed with water and the organic phase was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (using an Isolute column, eluent: heptane/ethyl acetate gradient, 0-100%) to give tert-butyl 3-formylazetidine-1-carboxylate (0.19 g, 27% yield). | [References]
[1] Patent: WO2014/165075, 2014, A1. Location in patent: Page/Page column 45; 46 [2] Patent: US2014/171402, 2014, A1. Location in patent: Paragraph 0053; 0054; 0055; 0056 [3] Patent: EP2754653, 2014, A2. Location in patent: Paragraph 0044; 0045 [4] Patent: WO2018/89355, 2018, A1. Location in patent: Page/Page column 102-104 [5] Patent: WO2010/80357, 2010, A1. Location in patent: Page/Page column 45-46 |
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