Bromide ion → t-Butyl (1R)-1-(4-(2-methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethylcarbamate

HRID 454982Notes

Reaction equation

[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br-]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:8][CH:17]([CH3:22])[CH2:18][CH2:19][CH3:20])=[CH:21][CH:22]=1)[CH2:9][N:10]1[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of [(R)-1-(4-hydroxy-phenyl)-2-(4-methyl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester (57 mg, 0.17 mmol), K2CO3 (72 mg, 0.52 mmol) and 2-methylpenthyl bromide (60 ul, 0.42 mmol) in DMF (1 ml) was stirred at 55° C. for over night. After cool to rt, the mixture was diluted with EtOAc and washed with H2O and dried (MgSO4). Removal of the solvent provided the titled compound. MS (MH+).

Workup

temperatureAfter cool to rt
washwashed with H2O
dry with materialdried (MgSO4)
customRemoval of the solvent

Sources & evidence

ORD record: ord-79db1b79f5d5410a828e622afbb15db1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497271B2

Reaction notes

Loading…