(2S,3S)-N-cyclopropyl-3-(dibenzylamino)-2-hydroxyhexanamide → (2S,3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamide
Reaction equation
[CH:1]1([NH:4][C:5](=[O:27])[C@@H:6]([OH:26])[C@@H:7]([N:11](CC2C=CC=CC=2)CC2C=CC=CC=2)[CH2:8][CH2:9][CH3:10])[CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[NH2:11][C@@H:7]([CH2:8][CH2:9][CH3:10])[C@H:6]([OH:26])[C:5]([NH:4][CH:1]1[CH2:2][CH2:3]1)=[O:27]Participants
4
Procedure
To a solution of (2S,3S)-N-cyclopropyl-3-(dibenzylamino)-2-hydroxyhexanamide (35.0 g) in methanol (350 mL) was carefully added palladium hydroxide on carbon (20% Pd(OH)2/C, 7.0 g), and the mixture was stirred under hydrogen at 50 psi for 2 hours. The mixture was filtered through Celite, and washed with methanol (150 mL). The solvent was evaporated under reduced pressure, to provide a light yellow solid, which was further washed with hexanes (2×75 mL), to give (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide (16.4 g).
Workup
- filtrationThe mixture was filtered through Celite
- washwashed with methanol (150 mL)
- customThe solvent was evaporated under reduced pressure
- customto provide a light yellow solid, which
- washwas further washed with hexanes (2×75 mL)
Sources & evidence
- ORD record
- ord-fc9d0d08766b467484aa9078b31efe69
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431733B2
Reaction notes
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