(3R,4S,5S,6S)-5-(5-isopropyl-2-methoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxylic acid dihydrochloride → (3R,4S,5S,6S)-5-amino-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxylic acid dihydrochloride

HRID 1599445Notes

Reaction equation

HRID 1599445 reaction equation
[ClH:1].Cl.C(C1C=CC(OC)=C(C=1)C[NH:12][C@@H:13]1[C@H:18]([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]2[CH2:32][CH2:33][C@H:14]1[C@@H:15]([C:34]([OH:36])=[O:35])[CH2:16]2)(C)C>O.[Pd]>[ClH:1].[ClH:1].[NH2:12][C@@H:13]1[C@H:18]([CH:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]2[CH2:32][CH2:33][C@H:14]1[C@@H:15]([C:34]([OH:36])=[O:35])[CH2:16]2

Participants

4

Reactant 1

HCID 70115624(3R,4S,5S,6S)-5-(5-isopropyl-2-methoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxylic acid dihydrochloride

Product 1

HCID 70145403(3R,4S,5S,6S)-5-amino-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxylic acid dihydrochlorideYield 111.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of (3R,4S,5S,6S)-5-(5-isopropyl-2-methoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxylic acid dihydrochloride (500 mg, 0.88 mmol) and Pd-C (10%, 500 mg) in water (20 mL) was stirred under H2 atmosphere (50 atm) at rt for 20 h. The catalyst was filtered off by filtration, and the filtrate was concentrated to give the title compound as a pale yellow solid (200 mg, 0.49 mmol, 54%).

Workup

  1. filtrationThe catalyst was filtered off by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-975895ffb95c4a79bc3b4582f7cdefef
Source dataset
uspto-grants-1998_04
Patent number
US05741797

Reaction notes

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