(1R,3S,5R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid → (1R,3S,5R)-tert-butyl 3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14](O)=[O:15])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][OH:15])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
To a solution of (1R,3S,5R)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester (0.5 g, 2.2 mmol) in dry THF (10 mL), cooled to 0° C., was added under an argon atmosphere dropwise a 1M solution of boran-tetrahydrofuran-complex (4.40 mL, 4.40 mmol). The reaction mixture was kept at 0° C. for an additional 2 h and then allowed to warm up to RT overnight. The reaction was quenched by careful addition of water and subsequently EtOAc. The organic layer was subsequently washed with saturated aqueous solutions of NaCl, NaHCO3, water and NaCl. The organic phase was dried (phase separator) and concentrated to give the title compound as a colorless oil. MS (LC-MS): 214.0 [M+H]+; tR (HPLC conditions k): 2.99 min. The material thus obtained was used in the next step without further purification.
Workup
- customThe reaction was quenched by careful addition of water and subsequently EtOAc
- washThe organic layer was subsequently washed with saturated aqueous solutions of NaCl, NaHCO3, water and NaCl
- customThe organic phase was dried (phase separator)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ef82d357379f48e591619177a5b81af2
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085555B2
Reaction notes
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