HCID 86679681, compound → HCID 86679682, compound

HRID 928207Notes

Reaction equation

HRID 928207 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>CO.[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 41.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (+/−)-cis-tert-butyl 5-benzyl-3a-methoxyhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (1.5 g, 4.5 mmol) in MeOH (100 mL) was added Pd(OH)2/C (300 mg) under nitrogen. The suspension was degassed under vacuum and purged with hydrogen three times. The mixture was stirred at 40-50° C. under hydrogen (45 psi) overnight. TLC (petroleum ether/EtOAc=2/1) showed the reaction was complete. The mixture was filtered, concentrated and purified by column chromatography (CH2Cl2/MeOH=15/1) to afford the title compound (454 mg, 41% yield) as a yellow gum. 1H NMR (400 MHz, CDCl3) δ 3.95 (brs., 2 H), 3.51-3.78 (m, 3 H), 3.36-3.50 (m, 2 H), 3.14-3.35 (m, 4 H), 2.83-3.08 (m, 2 H), 2.75 (brs., 1 H), 1.45 (s, 9 H). m/z (APCI+) for C12H22N2O3 [M−56+H]+.

Workup

  1. customThe suspension was degassed under vacuum
  2. custompurged with hydrogen three times
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. custompurified by column chromatography (CH2Cl2/MeOH=15/1)

Sources & evidence

ORD record
ord-19b5d98f51524d839d7af8e2f02dd9c0
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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