(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → 1,1-Dimethylethyl N-[(3R)-1-(5-bromo-2-pyridinyl)-3-pyrrolidinyl]carbamate

HRID 423398Notes

Reaction equation

HRID 423398 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[C:9]([O:13][C:14](=[O:21])[NH:15][C@@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)([CH3:12])([CH3:11])[CH3:10]>>[C:9]([O:13][C:14](=[O:21])[NH:15][C@@H:16]1[CH2:20][CH2:19][N:18]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:17]1)([CH3:12])([CH3:10])[CH3:11]

Participants

3

Reactant 2

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 574567861,1-Dimethylethyl N-[(3R)-1-(5-bromo-2-pyridinyl)-3-pyrrolidinyl]carbamateYield 30.9%

Procedure

Prepare the title compound by essentially following the procedure as described for Preparation 49, using 5-bromo-2-fluoro-pyridine (6.26 g, 35.61 mmol), and (R)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (6.632 g, 35.61 mmol) to give 3.77 g (30%) of the title compound. LC-MS/ES m/z (81Br) 344.3 [M+H]+.

Workup

  1. customas described for Preparation 49

Sources & evidence

ORD record
ord-3ff009574aa44a78a78b2e3cec8a11c9
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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