HCID 67130703, compound → HCID 67130930, compound

HRID 73595Notes

Reaction equation

HRID 73595 reaction equation
COC1C=CC(C[N:8]2[CH2:13][C@H:12]([CH3:14])[C@H:11]3[O:15][C:16](=[O:18])[NH:17][C@@H:10]3[CH2:9]2)=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:14][C@H:12]1[CH2:13][NH:8][CH2:9][C@H:10]2[NH:17][C:16](=[O:18])[O:15][C@H:11]12

Participants

4

Reactant 1

HCID 67130703HCID 67130703, compound

Product 1

HCID 67130930HCID 67130930, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3aR,7S,7aR)-5-(4-methoxybenzyl)-7-methylhexahydrooxazolo[4,5-c]pyridin-2(3H)-one (1.0 equiv.) in methanol, at a concentration of 0.1M, was added 20% palladium hydroxide on carbon (0.3 eq.). The resultant heterogeneous solution was put under an atmosphere of hydrogen and was stirred for 2 hours. At this time the mixture was filtered through a pad of celite eluting with methanol. The volatiles were removed in vacuo yielding (3aR,7S,7aR)-7-methylhexahydrooxazolo[4,5-c]pyridin-2(3H)-one (99%). LCMS (m/z): 157.1 (MH+).

Workup

  1. filtrationAt this time the mixture was filtered through a pad of celite
  2. washeluting with methanol
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-c516915896474a09b41b4dbfd8a106fd
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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