Ammonium formate → 3-(SR)-(4-(2-tolyl)-piperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidine

HRID 1276509Notes

Reaction equation

HRID 1276509 reaction equation
C([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[CH2:22][CH2:21]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd].[OH-].[OH-].[Pd+2]>[C:27]1([CH3:32])[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH:23]1[CH2:24][CH2:25][N:20]([CH2:19][CH:10]2[CH:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:12][NH:8][CH2:9]2)[CH2:21][CH2:22]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 701994401-Benzyl-3-(SR)-(4-(2-tolyl)-piperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidine

Product 1

HCID 702004833-(SR)-(4-(2-tolyl)-piperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared from 15 mg of 1-Benzyl-3-(SR)-(4-(2-tolyl)-piperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidine (from Example 20), 35 mg of ammonium formate and 8 mg of 10% Pd on carbon in 1.5 mL of MeOH using a procedure analogous to that described in Example 30, Step A (except Pd on carbon was substituted for 20% Pd(OH)2) to provide the title compound, which was taken onto Step B without further purification.

Sources & evidence

ORD record
ord-d405090328464c60b3efe8a7c71cacd6
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

Loading…