1-[(5-Bromo-2-thienyl)carbonyl]pyrrolidine → [2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-{4-[5-(pyrrolidine-1-carbonyl)-thiophen-2-yl]-phenyl}-methanone

HRID 646438Notes

Reaction equation

HRID 646438 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=1)=[O:14].Br[C:31]1[S:35][C:34]([C:36]([N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:37])=[CH:33][CH:32]=1>>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:31]2[S:35][C:34]([C:36]([N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)=[O:37])=[CH:33][CH:32]=2)=[CH:17][CH:16]=1)=[O:14]

Participants

3

Reactant 2

HCID 12465611-[(5-Bromo-2-thienyl)carbonyl]pyrrolidineHCID 57980025[2-(S)-(2-(R)-Methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

Product 1

HCID 11669612[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-{4-[5-(pyrrolidine-1-carbonyl)-thiophen-2-yl]-phenyl}-methanoneYield 34%

Procedure

The title compound is prepared in a manner substantially analogous to General Procedure A using [2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone (398 mg, 1.0 mmol) and (5-Bromo-thiophen-2-yl)-pyrrolidin-1-yl-methanone (CAS 326875-64-3) 261 mg, 1.0 mmol) to give 150 mg (34% yield). MS (ES+) 452.2 (M+H)+

Workup

  1. customto give 150 mg (34% yield)

Sources & evidence

ORD record
ord-77a6d934845540e79291399e985a3dd0
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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