HCID 86679681, compound → HCID 86679682, compound

HRID 577756Notes

Reaction equation

HRID 577756 reaction equation
C([N:8]1[CH2:12][C@:11]2([O:23][CH3:24])[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@H:10]2[CH2:9]1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH3:24][O:23][C@@:11]12[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@H:10]1[CH2:9][NH:8][CH2:12]2

Participants

4

Reactant 1

HCID 86679681HCID 86679681, compound

Product 1

HCID 86679682HCID 86679682, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl(cis)-5-benzyl-3a-methoxyhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (185 mg, 0.556 mmol) in EtOH (5.5 mL) purged with nitrogen was added Pd(OH)2/C (78 mg) and stirred under H2 (balloon) for 18 hrs. The reaction mixture was filtered and concentrated under reduced pressure to afford the title compound (128 mg, 95% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 3.83-4.02 (m, 1H) 3.38-3.80 (m, 5H) 3.34 (s, 3H) 3.14-3.33 (m, 2H) 2.78-3.05 (m, 2H) 1.47 (s, J=2.57 Hz, 9H); m/z (APCI+) for C12H22N2O3 243.20 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-18a974ff56ae4646b004b8d00c8498e8
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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