Reaction equation
[CH3:1][C:2]1([CH3:14])[N:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[C:4](=[O:13])[CH2:3]1.[BH4-].[Na+].O.[NH4+].[Cl-]>CO>[C:9]([O:8][C:6](=[O:7])[NH:5][C:2]([CH3:14])([CH3:1])[CH2:3][CH2:4][OH:13])([CH3:12])([CH3:10])[CH3:11]Participants
Procedure
4,4-Dimethyl-1-tert-butyloxycarbonyl-azetidine-2-one (32.5 g, synthesized according to Schoen et al., J. Med. Chem. 1994, 37 (7), 897) was dissolved in methanol (450 ml). The solution was cooled to 0° by means of an ice bath and treated with sodium borohydride (18.3 g, 6 portions over 45 minutes). The mixture was allowed to stir for 3 hours at 0°, warmed to room temperature and stirred for another 60 min. The reaction mixture was then poured into a mixture of ice, water and sat. NH4Cl solution and extracted with ether. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residual oil was purified by flash chromatography (gradient of hexanes in ethyl acetate: 7/3 to 1/1). The fractions containing the product were combined, evaporated and dried in vacuo to leave a colorless oil (26.7 g).
Workup
- temperatureThe solution was cooled to 0° by means of an ice bath
- stirringstirred for another 60 min
- extractionextracted with ether
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over Na2SO4
- customevaporated
- customThe residual oil was purified by flash chromatography (gradient of hexanes in ethyl acetate: 7/3 to 1/1)
- additionThe fractions containing the product
- customevaporated
- customdried in vacuo
Sources & evidence
- ORD record
- ord-c44853381de24de9bd6c2849b282127a
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07314884B2
Linked notes
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