Benzene, 1-bromo-4-(trifluoromethyl)- → {(2s,4r)-1-{Bis[4-(trifluoromethyl)phenyl]methyl}-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

HRID 1869772Notes

Reaction equation

HRID 1869772 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C[CH:13]([C@@H:17]1[CH2:22][CH2:21][NH:20][C@H:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH2:18]1)[C:14]([O-:16])=[O:15]>>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([CH:19]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=2)[N:20]2[CH2:21][CH2:22][C@@H:17]([CH2:13][C:14]([OH:16])=[O:15])[CH2:18][C@H:19]2[C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=2)=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 86617999(+)-methyl{(2S,4R)-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

Product 1

HCID 57987491{(2s,4r)-1-{Bis[4-(trifluoromethyl)phenyl]methyl}-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

Procedure

The compound was prepared analogously to Example 160 using the Grignard reagent derived from 4-brombenzotrifluoride and starting with the chiral piperidine of Example 114 Step 1. M/Z (ES+) 590 (M+H).

Sources & evidence

ORD record
ord-067acc28a9ce4bf291ae259f7456294c
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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