1-Bromo-3-methoxypropane → {(2s,4r)-1-{(1r)-4-Methoxy-1-[4-(trifluoromethyl)phenyl]butyl}-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

HRID 1869771Notes

Reaction equation

HRID 1869771 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][CH3:6].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]>>[CH3:6][O:5][CH2:4][CH2:3][CH2:2][C@@H:14]([N:15]1[CH2:16][CH2:17][C@@H:12]([CH2:8][C:9]([OH:11])=[O:10])[CH2:13][C@H:14]1[C:18]1[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=1)[C:18]1[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 5245511-Bromo-3-methoxypropaneHCID 86617999(+)-methyl{(2S,4R)-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

Product 1

HCID 57987584{(2s,4r)-1-{(1r)-4-Methoxy-1-[4-(trifluoromethyl)phenyl]butyl}-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

Procedure

The compound was prepared analogously to Example 160 using the Grignard reagent derived from 1-bromo-3-methoxypropane and starting with the chiral piperidine of Example 114 Step 1. M/Z (ES+) 518 (M+H).

Sources & evidence

ORD record
ord-ff2adef1b22f4977ba37e25fadda465b
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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