Triethylamine → HCID 66727759, compound

HRID 2409177Notes

Reaction equation

HRID 2409177 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH:7]1[CH2:8][CH2:9][C:10]2=[O:12])=[O:5])[CH3:2].CCN(CC)CC.O([Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])S(C(F)(F)F)(=O)=O>ClCCl>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH:7]1[CH2:8][CH:9]=[C:10]2[O:12][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 565357Ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate

Product 1

HCID 66727759HCID 66727759, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of (1RS,5SR,6RS)-2-oxo-bicyclo[3,1,0]hexane-6-carboxylic acid ethyl ester (28.93 g, 172 mmole) in dichloromethane (430 ml) was added at 22° C. NEt3 (36.0 ml, 258 mmole), the mixture was cooled to 0° C. and treated with tert-butyldimethylsilyl triflate (43.5 ml, 189.2 mmole) keeping the temperature below 10° C. The mixture was allowed to warm to 22° C. over 2 h, washed with saturated aqueous NaHCO3, the organic layer was dried, evaporated and the residue purified over aluminiumoxide (100 g) using cyclohexane/AcOEt (9:1) to give the title compound as a yellow oil which was used without further purification in the next step.

Workup

  1. customthe temperature below 10° C
  2. washwashed with saturated aqueous NaHCO3
  3. customthe organic layer was dried
  4. customevaporated
  5. customthe residue purified over aluminiumoxide (100 g)

Sources & evidence

ORD record
ord-f5efdb3012f949adb2b7ef234d134c81
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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