2-Bromopyridine → tert-Butyl N-[(3S)-1-(pyridin-2-yl)pyrrolidin-3-yl]carbamate

HRID 1696968Notes

Reaction equation

[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred solution comprising (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (2.0 g, 10.7 mmol), 2-bromopyridine (1.7 g, 10.7 mmol) and TEA (1.1 g, 10.7 mmol) in DMF (40 ml) is heated to 80° C. for 50 hours. The solvent is removed in vacuo the purification of the crude residue by chromatography on silica eluting with ethyl acetate:hexane (1:9 increasing to 1:4) yields the titled compound as a white solid.

Workup

customThe solvent is removed in vacuo
customthe purification of the crude residue by chromatography on silica eluting with ethyl acetate:hexane (1:9 increasing to 1:4)

Sources & evidence

ORD record: ord-942a0e0910e0444aa1d9b9f1262d8e93
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163754B2

Reaction notes

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