Ammonium Hydroxide → HCID 54361786, compound

HRID 618181Notes

Reaction equation

HRID 618181 reaction equation
C([N:8]1[CH2:12][C@@H:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:10]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9]1)C1C=CC=CC=1.[OH-].[NH4+]>CO.[OH-].[OH-].[Pd+2]>[CH2:14]([O:13][C@H:11]1[C@H:10]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9][NH:8][CH2:12]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 54196415HCID 54196415, compound

Product 1

HCID 54361786HCID 54361786, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3R,4R)-1-benzyl-3,4-dibenzyloxypyrrolidine (26.8 g, 71.7 mmol) in methanol (600 ml) was added palladium hydroxide on activated charcoal (20% Pd, 2,7 g) and 25% ammonium hydroxide (6 ml). The mixture was hydrogenated in a Parr apparatus at 20 psi for 20 hours. The mixture was filtered and evaporated to dryness in vacuo to give (3R,4R)-3,4-dibenzyloxypyrrolidine (19.7 g, yield: 96%) as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-aa63e8cd14444982913641e149a67b24
Source dataset
uspto-grants-1999_09
Patent number
US05952363

Reaction notes

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