Ethyl diazoacetate → 4-(Tert-butyl-diphenyl-silanyloxy)-bicyclo[5.1.0]octane-8-carboxylic acid ethyl ester

HRID 16227

Reaction equation

HRID 16227 reaction equation
[C:1]([Si:5]([O:18][CH:19]1[CH2:25][CH2:24][CH:23]=[CH:22][CH2:21][CH2:20]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N-]>ClCCl>[CH2:32]([O:31][C:29]([CH:28]1[CH:22]2[CH:23]1[CH2:24][CH2:25][CH:19]([O:18][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:20][CH2:21]2)=[O:30])[CH3:33]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 67512396Tert-butyl-(cyclohept-4-enyloxy)-diphenyl-silane

Product 1

HCID 686886034-(Tert-butyl-diphenyl-silanyloxy)-bicyclo[5.1.0]octane-8-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 8C (2.2 g, 6.28 mmoles) and Rh2(OAc)4 (2 mg, 4.3 μmol) in dichloromethane (2 mL), ethyl diazoacetate (0.717 g, 6.28 mmoles) in dichloromethane (4 mL) was added over two hours via a syringe pump. The solvent was evaporated in vacuo and product purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 80:20) to provide the title compound.

Workup

  1. customThe solvent was evaporated in vacuo and product
  2. custompurified by flash column chromatography (hexanes:ethyl acetate 100:0 to 80:20)

Sources & evidence

ORD record
ord-e40caf334b0742ffaf4ef4909375fc79
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Linked notes

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