Ethyl 2-bromo-2-cyclopropylacetate → Ethyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)-2-cyclopropylacetate

HRID 932199Notes

Reaction equation

HRID 932199 reaction equation
[CH2:1]([C@@:4]1([CH3:25])[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[CH:27]([CH:33]1[CH2:35][CH2:34]1)[C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[CH2:1]([C@@:4]1([CH3:25])[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]([CH:27]([CH:33]2[CH2:35][CH2:34]2)[C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:5]1=[O:24])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 44222804Ethyl 2-bromo-2-cyclopropylacetateHCID 58574008(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one

Product 1

HCID 68000455Ethyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)-2-cyclopropylacetate

Procedure

Coupling of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one (Example 71, Step D) and ethyl 2-bromo-2-cyclopropylacetate (Example 249, Step A) using the procedure as described in Example 9, step A afforded the title compound as a mixture of two diastereomers.

Sources & evidence

ORD record
ord-05c5f4b6ad0045adb86c0b90b0b96688
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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