Tetrahydrofuran → (1S,5R)-5-Hydroxymethyl-2-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.2.0]heptane-1-carboxylic acid methyl ester

HRID 1917317Notes

Reaction equation

HRID 1917317 reaction equation
[CH3:1][O:2][C:3]([C@@:5]12[CH2:11][CH2:10][C@:9]1([CH2:12][O:13]CC1C=CC=CC=1)[CH2:8][N:7]([C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22])[C:6]2=[O:29])=[O:4].O1CCCC1.[H][H]>[C].[Pd].C(O)C>[CH3:1][O:2][C:3]([C@@:5]12[CH2:11][CH2:10][C@:9]1([CH2:12][OH:13])[CH2:8][N:7]([C@@H:21]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:22])[C:6]2=[O:29])=[O:4]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 67490760(1S,5R)-5-Benzyloxymethyl-2-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.2.0]heptane-1-carboxylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 67490818(1S,5R)-5-Hydroxymethyl-2-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.2.0]heptane-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A 10% palladium-carbon catalyst (50% wet, 200 mg) was added to a solution of (1S,5R)-5-benzyloxymethyl-2-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.2.0]heptane-1-carboxylic acid methyl ester (1.82 g, 4.62 mmol) in ethanol (20 mL)-tetrahydrofuran (20 mL), and the mixture was stirred in a hydrogen atmosphere at 40° C. for 2.5 hours. After removing the catalyst by filtration, the filtrate was concentrated to give the title compound as colorless crystals.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c9d9ddfd293b41ba805e54b25f77bb79
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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