Ethyl diazoacetate → Ethyl 3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexane-6-carboxylate

HRID 2203663Notes

Reaction equation

HRID 2203663 reaction equation
[C:1]([Si:5]([O:18][CH:19]1[CH2:23][CH:22]=[CH: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:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N-]>ClCCl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[Si:5]([O:18][CH:19]1[CH2:23][CH:22]2[CH:21]([CH:26]2[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:20]1)([C:1]([CH3:4])([CH3:2])[CH3:3])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 11347853Tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane

Product 1

HCID 123888938Ethyl 3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexane-6-carboxylateYield 538%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane (0.100 kg, 310 mmol) and rhodium acetate dimer (1.37 g, 3.10 mmol) in anhydrous dichloromethane (1.2 L) at room temperature was added a solution of ethyl 2-diazoacetate (63.68 mmol) in dichloromethane (300 mL) over 8 h. After an additional 12 h. The reaction mixture was filtered through Celite. Concentration of the filtrate afforded crude ethyl 3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexane-6-carboxylate (140 g) which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through Celite

Sources & evidence

ORD record
ord-2be6d76b50344e208d0fdd3e144515d6
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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