(Bromomethyl)cyclopentane → (3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopentylmethyl)piperidin-2-one

HRID 931922Notes

Reaction equation

HRID 931922 reaction equation
[CH2:1]([C@@H:4]1[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[NH:6][C:5]1=[O:24])[CH:2]=[CH2:3].Br[CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH2:1]([C@@H:4]1[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([CH2:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:5]1=[O:24])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 12723264(Bromomethyl)cyclopentaneHCID 58573283(3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one

Product 1

HCID 67999125(3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopentylmethyl)piperidin-2-one

Procedure

The title compound was prepared from (3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one (Example 42, Step A) and (bromomethyl)cyclopentane as described in Example 44, Step A. Purification of the residue by silica gel prep plate (25% EtOAc/hexanes) provided the title compound as a colorless solid.

Workup

  1. customPurification of the residue by silica gel prep plate (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-470073929b2341a69a00c0d09cdeab42
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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