Ammonia → 4'-((1S,2S)-2-{[(2R)-2-Methylpyrrolidin-1-yl]methyl}cyclopropyl)-1,1'-biphenyl-4-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	1-{[(1S,2S)-2-(4-bromophenyl)cyclopropyl]methyl}-(2S)-2-methylpyrrolidine	HCID 57515375	—
Reactant	(R)-1-(((1S,2S)-2-(4-bromophenyl)cyclopropyl)methyl)-2-methylpyrrolidine	HCID 66796087	—
Product	4'-((1S,2S)-2-{[(2R)-2-Methylpyrrolidin-1-yl]methyl}cyclopropyl)-1,1'-biphenyl-4-carbonitrile	HCID 44199138	—

Reaction Steps

The title compound was prepared using the procedure described in Example 1E substituting 1-[2-(4-bromo-phenyl)-(1S,2S)-cyclopropylmethyl]-(2R)-2-methyl-pyrrolidine (the product from Example 2A) for 1-[(1S,2S)-2-(4-bromo-phenyl)-cyclopropylmethyl]-2(S)-methyl-pyrrolidine (the product from 1D). 1H NMR (300 MHz, CD3OD): 0.92 (m, 1H), 0.99 (m, 1H), 1.13 (d, J=6 Hz, 2H), 1.24 (m, 1H), 1.43 (m, 1H), 1.77 (m, 3H), 1.98 (m, 2H), 2.13 (dd, J=12 Hz, J=6 Hz, 1H), 2.30 (q, J=9 Hz, 1H), 2.41 (m, 1H), 2.94 (dd, J=12 Hz, J=6 Hz, 1H), 3.25 (m, 1H), 7.00 (d, J=9 Hz, 2H), 7.36 (d, J=9 Hz, 2H) MS (DCl—NH3) m/z 294 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08829041B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-9ff9efbff17945e8a9aee5df46190c64
Source note	uspto-grants-2014_09