1,1-Dimethylethyl[[3-[1-(phenylmethyl)-3-pyrrolidinyl]phenyl]methyl]carbamate → 1,1-Dimethylethyl [[3-(3-pyrrolidinyl)phenyl]methyl]-carbamate

HRID 54468Notes

Reaction equation

HRID 54468 reaction equation
CC([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]2[CH2:20][CH2:19][N:18](CC3C=CC=CC=3)[CH2:17]2)[CH:11]=1)[C:6](=[O:8])[O-:7])(C)C>[Pd].CO>[NH:18]1[CH2:19][CH2:20][CH:16]([C:12]2[CH:11]=[C:10]([CH2:9][NH:5][C:6](=[O:8])[O:7][C:10]([CH3:15])([CH3:11])[CH3:9])[CH:15]=[CH:14][CH:13]=2)[CH2:17]1

Participants

4

Reactant 1

HCID 867507241,1-Dimethylethyl[[3-[1-(phenylmethyl)-3-pyrrolidinyl]phenyl]methyl]carbamate

Product 1

HCID 540659501,1-Dimethylethyl [[3-(3-pyrrolidinyl)phenyl]methyl]-carbamateYield 175.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1,1-dimethylethyl[[3-[1-(phenylmethyl) -3-pyrrolidinyl]phenyl]methyl]carbamate (4.50 g, 12.3 mmol) and 20% palladium on charcoal catalyst (0.30 g) in methanol (100 mL) was hydrogenated in a Parr apparatus at 3 atm. The suspension was filtered through a pad of Celite and the filtrate concentrated to give an orange oil. This oil was chromatographed (silica gel, dichloromethane-methanol 1:1 containing 1% ammonia) to give the title compound (2.99 g, 88%) as a pale yellow oil.

Workup

  1. filtrationThe suspension was filtered through a pad of Celite
  2. concentrationthe filtrate concentrated
  3. customto give an orange oil
  4. customThis oil was chromatographed (silica gel, dichloromethane-methanol 1:1 containing 1% ammonia)

Sources & evidence

ORD record
ord-05c4b9114b424097af1f81c0bac0f68c
Source dataset
uspto-grants-1997_04
Patent number
US05622966

Reaction notes

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