Acetic Acid → (7R,8aS)-4-benzhydryl-7-[(tert-butyldimethylsilyl)oxy)octahydropyrrolo[1,2-a]pyrazine

HRID 1006336Notes

Reaction equation

HRID 1006336 reaction equation
C([N:8]([CH2:25][C@@H:26]1[CH2:30][C@@H:29]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:28][N:27]1C([O-])=O)[CH2:9][C:10](=O)[CH:11](C1C=CC=CC=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C1C=CC=CC=1.[C:42](O)(=O)[CH3:43]>CO.[Pd]>[CH:11]([CH:10]1[N:27]2[CH2:28][C@H:29]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:30][C@H:26]2[CH2:25][NH:8][CH2:9]1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:43]1[CH:42]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86589637(2S,4R)-2-[[N-benzyl-N-(2-oxo-3,3-diphenylpropyl)amino]methyl]-4-[(tert-butyldimethylsilyl)oxy]-1-pyrrolidinecarboxylate

Product 1

HCID 69818675(7R,8aS)-4-benzhydryl-7-[(tert-butyldimethylsilyl)oxy)octahydropyrrolo[1,2-a]pyrazineYield 227.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2S,4R)-2-[[N-benzyl-N-(2-oxo-3,3-diphenylpropyl)amino]methyl]-4-[(tert-butyldimethylsilyl)oxy]-1-pyrrolidinecarboxylate (4.82 g) and acetic acid (0.87 g) in methanol (100 ml) was hydrogenated over 10% palladium-charcoal (50% wet, 1.0 g) at room temperature under 2-3 atoms for 15 hours. After removal of the catalyst by filtration, the filtrate was evaporated under reduced pressure to give bis(acetic acid) salt of (7R,8aS)-4-benzhydryl-7-[(tert-butyldimethylsilyl)oxy]octahydropyrrolo[1,2-a]pyrazine (4.05 g) as a syrup.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-54eb0632545d4715986e63e82de6477e
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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