HCID 67092641, compound → HCID 67093351, compound

HRID 1261840Notes

Reaction equation

HRID 1261840 reaction equation
C(OC([N:11]1[C@@H:16]([CH3:17])[C:15](=[O:18])[N:14]2[C@@H:19]([CH2:22][CH2:23][CH2:24][N:25]3[CH2:32][CH2:31][C:28]4([CH2:30][CH2:29]4)[C@H:27]([OH:33])[CH2:26]3)[CH2:20][O:21][C:13]2([CH3:34])[CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[OH:33][C@@H:27]1[CH2:26][N:25]([CH2:24][CH2:23][CH2:22][C@@H:19]2[N:14]3[C:15](=[O:18])[C@H:16]([CH3:17])[NH:11][CH2:12][C:13]3([CH3:34])[O:21][CH2:20]2)[CH2:32][CH2:31][C:28]21[CH2:30][CH2:29]2

Participants

4

Reactant 1

HCID 67092641HCID 67092641, compound

Product 1

HCID 67093351HCID 67093351, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3S,6S)-3-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-6,8a-dimethyl-5-oxo-hexahydro-oxazolo[3,2-a]pyrazine-7-carboxylic acid benzyl ester (295 mg, 0.63 mmol) in MeOH (3 mL) was stirred for 1½ h at room temperature under a hydrogen atmosphere (1 bar) in the presence of palladium (10% on activated charcoal, 133 mg), then insoluble material was removed by filtration through diatomaceous earth. The filtrate was evaporated to afford the title compound (208 mg, 99%) Colourless gum, MS (ISP)=338.3 (M+H)+.

Workup

  1. custominsoluble material was removed by filtration through diatomaceous earth
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-62aecd5e25bc40b7b7881e61160cbcde
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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