Pyrrolidine → [4'-(Pyrrolidine-1-carbonyl)-biphenyl-4-yl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

HRID 1867799Notes

Reaction equation

HRID 1867799 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:9])=[CH:4][CH:3]=1.CO[C:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)=[O:24].[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>>[N:34]1([C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:2]3[CH:7]=[CH:6][C:5]([C:8]([N:10]4[CH2:14][CH2:13][CH2:12][C@H:11]4[CH2:15][N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)=[O:9])=[CH:4][CH:3]=3)=[CH:27][CH:26]=2)=[O:24])[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 27343694-Methoxycarbonylphenylboronic acidHCID 11965129Pyrrolidine, 1-(4-bromobenzoyl)-2-(1-pyrrolidinylmethyl)-, (2S)-

Product 1

HCID 57980167[4'-(Pyrrolidine-1-carbonyl)-biphenyl-4-yl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

Procedure

The title compound is prepared starting with (4-Bromo-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-yl)methanone and 4-methoxycarbonylphenyl boronic acid perform procedures significantly analogous to those found in Procedures BB, V′, W′ (with pyrrolidine in place of (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine) and Q. MS (m/e): 432.4 (M+1)

Sources & evidence

ORD record
ord-51288a2e110440c4995c42f022ba8379
Source dataset
uspto-grants-2009_12
Patent number
US07632857B2

Reaction notes

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