(3-Bromo-2,6-difluorophenyl)methanol → cis-2,6-Dimethyl-piperazine-1,4-dicarboxylic acid 1-(3-bromo-2,6-difluoro-benzyl) ester 4-tert-butyl ester

HRID 1794134Notes

Reaction equation

[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH2:9][OH:10])[C:5]([F:8])=[CH:6][CH:7]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][C@H:23]([CH3:25])[N:22]([C:26](Cl)=[O:27])[C@H:21]([CH3:29])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>>[Br:1][C:2]1[C:3]([F:11])=[C:4]([C:5]([F:8])=[CH:6][CH:7]=1)[CH2:9][O:10][C:26]([N:22]1[C@H:23]([CH3:25])[CH2:24][N:19]([C:17]([O:16][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:18])[CH2:20][C@@H:21]1[CH3:29])=[O:27]

Participants

Reactant 2

HCID 22219889(3-Bromo-2,6-difluorophenyl)methanol

HCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69141723cis-2,6-Dimethyl-piperazine-1,4-dicarboxylic acid 1-(3-bromo-2,6-difluoro-benzyl) ester 4-tert-butyl ester

Procedure

The compound was prepared from (3-bromo-2,6-difluoro-phenyl)-methanol and 4-chlorocarbonyl-cis-3,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester according to the procedures described in Example 121 and 54 to give the product as a colorless oil (9.75 g); MS (ISP): 482.3 (M+NH4)+.

Sources & evidence

ORD record: ord-8c0bbe66f86d411bb0fd0a66661aceb1
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022707B2

Reaction notes

Loading…