Hydrochloric Acid → HCID 86589641, compound

HRID 1006338Notes

Reaction equation

HRID 1006338 reaction equation
Cl.[N:2]([C@H:5]1[CH2:33][N:8]2[C@H:9]([CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][C@@H:7]2[CH2:6]1)=[N+]=[N-]>CO.[Pd]>[NH2:2][C@H:5]1[CH2:33][N:8]2[C@H:9]([CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:10][N:11]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:12][C@@H:7]2[CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86589642HCID 86589642, compound

Product 1

HCID 86589641HCID 86589641, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-charcoal (50% wet, 40 mg) and 0.1N hydrochloric acid (0.1 ml) were added into a solution of tert-butyl (4R,7R,8aS)-7-azido-4-benzhydrylhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (200 mg) in methanol (2.5 ml) at room temperature. The mixture was hydrogenated at room temperature under atmospheric pressure for 4 hours. The palladium was filtered and washed with methanol. The filtrate and washings were combined and concentrated in vacuo. The resulting residue was partitioned between aqueous sodium hydrogen carbonate and ethyl acetate. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography with a mixture of dichloromethane and methanol (15:1) as an eluent. The fractions containing the objective compound were collected to give tert-butyl (4R,7R,8aS)-7-amino-4-benzhydrylhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (193 mg).

Workup

  1. filtrationThe palladium was filtered
  2. washwashed with methanol
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was partitioned between aqueous sodium hydrogen carbonate and ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography with a mixture of dichloromethane and methanol (15:1) as an eluent
  9. additionThe fractions containing the objective compound
  10. customwere collected

Sources & evidence

ORD record
ord-733323157fd34797a41979d958fd1508
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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