Ammonium formate → tert-butyl (3aS,6aS)-1-(5-hydroxy-3-pyridinyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

HRID 1817021Notes

Reaction equation

HRID 1817021 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([N:15]2[CH2:19][CH2:18][C@H:17]3[CH2:20][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][C@@H:16]23)[CH:12]=[N:13][CH:14]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([N:15]2[CH2:19][CH2:18][C@H:17]3[CH2:20][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][C@@H:16]23)[CH:12]=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66757415(3aS,6aS)-tert-butyl 1-(5-(benzyloxy)pyridin-3-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Product 1

HCID 66757796tert-butyl (3aS,6aS)-1-(5-hydroxy-3-pyridinyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 82A (1.27 g, 3.21 mmol) in methanol (25 mL) was treated with ammonium formate (2.00 g, 30.2 mmol) and 10% Pd/C (0.27 g, wet). The mixture was warmed to reflux and allowed to stir for 20 hours. The reaction mixture was then allowed to cool to ambient temperature, filtered through Celite and the filtrate was concentrated under reduced pressure to provide the crude title compound which was taken on directly to the next step without further purification. MS (DCI/NH3) m/z 306 (M+H)+.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c4efc89a0efe42d2bc19091dc6457e5c
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

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