| Identification | More | [Name]
Boc-D-prolinol | [CAS]
83435-58-9 | [Synonyms]
BOC-D-PROLINOL
BOC-D-PRO-OL
BOC-(R)-2-(HYDROXYMETHYL) PYRROLIDINE
N-ALPHA-T-BOC-D-PROLINOL
N-BOC-D-PROLINOL
N-T-BOC-D-PROLINOL
N-T-BUTOXYCARBONYL-D-PROLINOL
N-TERT-BUTOXYCARBONYL-D-PROLINOL
(R)-(+)-1-BOC-2-PYRROLIDINEMETHANOL
(R)-1-BOC-2-PYRROLIDINEMETHANOL
(R)-(+)-1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINEMETHANOL
(R)-2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
(R)-(-)-N-BOC-PROLINOL
(R)-N-TERT-BUTOXYCARBONYL PROLINOL
1-BOC-D-PROLINOL
1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (2R)-
N-tert-Butoxycarbonyl-D-prolino
N-BENZYL-D-PROLINOL
N-alpha-t-Butyloxycarbonyl-D-prolinol, (R)-N-t-Butyloxycarbonyl-2-pyrrolidinemethanol
BOC-D-PROLINOL LIQUID | [EINECS(EC#)]
626-169-6 | [Molecular Formula]
C10H19NO3 | [MDL Number]
MFCD00040580 | [Molecular Weight]
201.26 | [MOL File]
83435-58-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White powder | [Melting point ]
60-64 °C (lit.) | [alpha ]
49 º (589nm, =1.3, CHCl3) | [Boiling point ]
289.5±13.0 °C(Predicted) | [density ]
1.084±0.06 g/cm3(Predicted) | [refractive index ]
54 ° (C=5, MeOH) | [storage temp. ]
Store at 0°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
14.77±0.10(Predicted) | [color ]
White to light beige | [Optical Rotation]
[α]23/D +50°, c = 1.3 in chloroform | [Water Solubility ]
insoluble | [InChI]
InChI=1S/C10H19NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h8,12H,4-7H2,1-3H3/t8-/m1/s1 | [InChIKey]
BFFLLBPMZCIGRM-MRVPVSSYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CCC[C@@H]1CO | [CAS DataBase Reference]
83435-58-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29051990 |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
N-(tert-Butoxycarbonyl)-D-prolinol is used to prepare (azetidinyl)methoxy]pyridines and 2-(aryloxymethyl) azacyclic analogs with therapeutic potetials for the treatment of central nervous system (CNS) disorders. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
Step 1: Dissolve (R)-2-(hydroxymethyl)pyrrolidine (2.0 g, 19.8 mmol) in dichloromethane (20 mL) and add 1 M aqueous sodium hydroxide solution (20 mL). A solution of di-tert-butyl dicarbonate (4.32 g, 19.8 mmol) in dichloromethane (10 mL) was added slowly and dropwise at room temperature. The reaction mixture was stirred at room temperature for 5 hours. After completion of the reaction, the organic and aqueous layers were separated. The organic layer was washed twice with distilled water and the aqueous layer was extracted with dichloromethane. All organic layers were combined and dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. Purification by recrystallization from hexane afforded the intermediate (R)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate in a yield of 2.60 g (65% yield). | [References]
[1] Patent: US5902819, 1999, A
[2] Patent: WO2006/19833, 2006, A1. Location in patent: Page/Page column 60
[3] European Journal of Organic Chemistry, 2002, # 14, p. 2391 - 2399
[4] Tetrahedron Letters, 1997, vol. 38, # 37, p. 6479 - 6482
[5] Tetrahedron Asymmetry, 1997, vol. 8, # 13, p. 2209 - 2213 |
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