1-Benzyl-3-nitro-4-phenylpyrrolidine → 1-Benzyl-4-phenylpyrrolidin-3-amine

HRID 588100Notes

Reaction equation

HRID 588100 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([N+:19]([O-])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N.[Ni]>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]([NH2:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 580091801-Benzyl-3-nitro-4-phenylpyrrolidine

Product 1

HCID 433170851-Benzyl-4-phenylpyrrolidin-3-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

To a stirred solution of (3S and R,4R and S)-1-benzyl-3-nitro-4-phenylpyrrolidine (100 g, 0.354 mol) in methanolic ammonia (1 L) was added Raney Ni (20 g) at room temperature in a 2.0 L hydrogenation flask. The reaction was hydrogenated at 100 psi for 12 h at room temperature. After completion of the reaction, the mixture was filtered through Celite and the filtrate was concentrated in vacuo to afford (3S and R,4R and S)-1-benzyl-4-phenylpyrrolidin-3-amine, which was carried onto the next step without further purification. MS ESI calc'd. For C12H20N2 [M+1]+ 253. found 253.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4f26f0c8a746462eab7725132e5d9656
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

Loading…