Boron trifluoride etherate → HCID 19783080, compound

HRID 257328Notes

Reaction equation

HRID 257328 reaction equation
O=C1CCCC1C(OC)=O.[F:11][C:12]1([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:15][CH2:14][C:13]1=[O:17].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>COCCOCCOC>[F:11][C:12]1([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:15][CH2:14][C:13]1=[O:17].[F:11][C:12]1([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:15][CH2:14][CH:13]1[OH:17]

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 516892Sodium BicarbonateHCID 11658332Cyclopentanecarboxylic acid, 1-fluoro-2-oxo-, methyl ester (9CI)

Product 2

HCID 11658332Cyclopentanecarboxylic acid, 1-fluoro-2-oxo-, methyl ester (9CI)HCID 19783080HCID 19783080, compoundYield 179%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
0 °C

Procedure

First, methyl 1-fluoro-2-oxocyclopentanecarboxylate was prepared from methyl 2-oxocyclopentanecarboxylate referring to the process described in Tetrahedron Letters 27 (37), 4465-4468 (1986). Then, 2.3 g (0.032 mol) of trimethylamine-borane complex and 5.0 g (0.031 mol) of the methyl 1-fluoro-2-oxocyclopentanecarboxylate were added to 50 ml of dry diglyme, the resulting solution was cooled to 0° C., and while it as stirred in the stream of nitrogen, 0.8 ml of boron trifluoride etherate was added dropwise. The resulting solution was stirred at room temperature for 1 hour and then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ether. The ether layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 4.5 g (yield: 89%) of the objective methyl 1-fluoro-2-hydroxycyclopentanecarboxylate in cis form (compound number 2a; the substance such that the substituent at the 2-position is supposed to take cis configuration when the methoxycarbonyl group at the 1-position is taken as a standard) which contains almost no the same in trans form.

Workup

  1. additionwas added dropwise
  2. extractionfollowed by extraction with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-ea5e9026acb0419f98a7cace79280272
Source dataset
uspto-grants-1993_11
Patent number
US05262385

Reaction notes

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