Diazo-acetic acid 4-(4-methoxy-benzyloxy)-but-2-enyl ester → (1R,5S,6S) 6-(4-methoxy-benzyloxymethyl)-3-oxa-bicyclo[3.1.0]hexan-2-one

HRID 1784056Notes

Reaction equation

HRID 1784056 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][CH2:9][CH:10]=[CH:11][CH2:12][O:13][C:14](=[O:18])[CH:15]=[N+]=[N-])=[CH:5][CH:4]=1>ClCCl>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][CH2:9][C@@H:10]2[C@@H:15]3[C@H:11]2[CH2:12][O:13][C:14]3=[O:18])=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 86604991Diazo-acetic acid 4-(4-methoxy-benzyloxy)-but-2-enyl ester

Product 1

HCID 68853945(1R,5S,6S) 6-(4-methoxy-benzyloxymethyl)-3-oxa-bicyclo[3.1.0]hexan-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1 g (3.6 mmol) of diazo-acetic acid 4-(4-methoxy-benzyloxy)-but-2-enyl ester in 50 ml dichloromethane under reflux were added within 8 hrs of 25 mg (0.03 mmol) of Rh2 (5S-MEPY)4 (Doyle dirhodium catalyst from Acros, CAS: 132435-65-5) dissolved in 100 ml of dichloromethane. Refluxing for another 20 hrs, evaporation of the solvent and chromatography on silica gel with heptane/AcOEt gave 850 mg (96%, >92% ee) of (1R,5S, 6S) 6-(4-methoxy-benzyloxymethyl)-3-oxa-bicyclo[3.1.0]hexan-2-one. Colorless oil. MS: 247 (M−H)−.

Workup

  1. temperatureRefluxing for another 20 hrs
  2. customevaporation of the solvent and chromatography on silica gel with heptane/AcOEt

Sources & evidence

ORD record
ord-15f35c06e96d498e9afbd4d1d1db75ea
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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