2-Bromoethyl methyl ether → HCID 66707757, compound

HRID 1690861Notes

Reaction equation

HRID 1690861 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][CH2:17][CH2:18]Br>C1CCCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:18][CH2:17][O:16][CH3:15])[CH:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 11063381tert-Butyl cyclohex-3-en-1-ylcarbamate

Product 1

HCID 66707757HCID 66707757, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

Cyclohex-3-enyl-carbamic acid tert-butyl ester (Kampferer, P.; Vasella, A. Helvetica Chimica Acta 2004, 87, 2764-2789) (3 g, 15.2 mmol) and 2-bromoethyl methyl ether (1.43 ml, 15.2 mmol) were treated overnight to the method of Example 7 Step A. After work up and chromatography of the reaction mixture (silica, cyclohexane/ethyl acetate=7/1) the title compound (Rf=0.33, 1.2 g, 31% yield) was obtained as colorless solid.

Sources & evidence

ORD record
ord-6d37bfc5cca14b218fc91f3042babf73
Source dataset
uspto-grants-2012_04
Patent number
US08153689B2

Reaction notes

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