Ammonium Chloride → rel-1,1-Dimethylethyl N-[[(1R,2R)-2-(hydroxymethyl)cyclobutyl]methyl]carbamate
Reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:8][CH2:7][C@H:6]1[CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=O.[BH4-].[Na+].[Cl-].[NH4+]>CO>[C:14]([O:13][C:11](=[O:12])[NH:10][CH2:9][C@@H:6]1[CH2:7][CH2:8][C@H:5]1[CH2:3][OH:2])([CH3:17])([CH3:15])[CH3:16]Participants
Procedure
To a solution of Trans-2-(tert-Butoxycarbonylamino-methyl)-cyclobutanecarboxylic acid methyl ester (4.1 g, 16.8 mmol) in methanol (20 mL) at 0° C., sodium Borohydride (1.3 g, 33.6 mmol) was added portionwise. The mixture was stirred 4 h until TLC after TLC indicated completion of the reaction. A saturated solution of ammonium chloride was added, the methanol was removed under vacuum and the water was extracted three times with dichloromethane. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, evaporated and purified with column chromatography on silica gel using n-Heptane-EtOAc (1:1). The product fractions were concentrated to give 2.8 g (16.8 mmol, 80% yield) of the title compound as a white solid. MS (m/e): 216.3 (M+H+)
Workup
- customcompletion of the reaction
- customthe methanol was removed under vacuum
- extractionthe water was extracted three times with dichloromethane
- washThe combined organic layers were washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- custompurified with column chromatography on silica gel
- concentrationThe product fractions were concentrated
Sources & evidence
- ORD record
- ord-b2c80cb7dea049e89501be10956b71cd
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039490B2
Reaction notes
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