4-Chlorobenzaldehyde → (2S,4R)-1-((1R)-1-(4-Chlorophenyl)-4-methylpentyl)-2-(4-(trifluoromethyl)phenyl)piperidine-4-acetic acid

HRID 1869773Notes

Reaction equation

Br[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].C[CH:8]([C@@H:12]1[CH2:17][CH2:16][NH:15][C@H:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[CH2:13]1)[C:9]([O-:11])=[O:10].[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1>>[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([C@H:33]([N:15]2[CH2:16][CH2:17][C@@H:12]([CH2:8][C:9]([OH:11])=[O:10])[CH2:13][C@H:14]2[C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=2)[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5])=[CH:31][CH:30]=1

Participants

Reactant 3

HCID 77264-Chlorobenzaldehyde

HCID 78911-Bromo-3-methylbutane

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

Product 1

HCID 57987388(2S,4R)-1-((1R)-1-(4-Chlorophenyl)-4-methylpentyl)-2-(4-(trifluoromethyl)phenyl)piperidine-4-acetic acid

Procedure

The compound was prepared analogously to Example 160 using the Grignard reagent derived from 1-bromo-3-methylbutane, starting with the chiral piperidine of Example 114 Step 1 and replacing 4-(trifluoromethyl)benzaldehyde with 4-chlorobenzaldehyde. M/Z (ES+) 482 (M+H).

Sources & evidence

ORD record: ord-376732b3025e466787239d5dca6a7987
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638629B2

Reaction notes

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