(S)-1-tert-butoxycarbonyl-2-methyl-3-oxo-4-benzylpiperazine → (S)-1-tert-butoxycarbonyl-2-methyl-4-benzylpiperazine

HRID 1596214Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10](=O)[C@@H:9]1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 45 °C

Procedure

To a stirred solution of (S)-1-tert-butoxycarbonyl-2-methyl-3-oxo-4-benzylpiperazine (1.0 g) in tetrahydrofuran (15 ml) was added borane-dimethylsulfide complex (0.49 ml) at 0° C. under nitrogen atmosphere. After stirring at 45° C. for 1.5 hours, borane-dimethylsulfide complex (0.46 ml) was added and the reaction mixture was stirred at 45° C. for another 2 hours. After cooled to 0° C., the reaction mixture was quenched with methanol. After evaporation of the solvent, the residue was purified by flash column chromatography eluting with a mixture of ethyl acetate and n-hexane (1:8) to give (S)-1-tert-butoxycarbonyl-2-methyl-4-benzylpiperazine (934 mg).

Workup

additionborane-dimethylsulfide complex (0.46 ml) was added
stirringthe reaction mixture was stirred at 45° C. for another 2 hours
temperatureAfter cooled to 0° C.
customthe reaction mixture was quenched with methanol
customAfter evaporation of the solvent
customthe residue was purified by flash column chromatography
washeluting with a mixture of ethyl acetate and n-hexane (1:8)

Sources & evidence

ORD record: ord-f4fbf0a87c6247ddb5e97a82fcfdaf70
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291464B1

Reaction notes

Loading…