Sodium Hydroxide → HCID 54541776, compound

HRID 257329Notes

Reaction equation

HRID 257329 reaction equation
[OH-].[Na+].[BH4-].[Na+].[CH3:5][O:6][C:7]([C:9]1([F:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:16])=[O:8]>CO>[CH3:5][O:6][C:7]([C:9]1([F:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[OH:16])=[O:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 53686142HCID 53686142, compound

Product 1

HCID 54541776HCID 54541776, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

25 ml of methanol was cooled to 5° C. and 70 mg (1.8 mmol) of sodium hydroxide and 0.14 g (3.7 mmol) of sodium borohydride were added. To the resulting solution was added dropwise in the range of 5° C. to 10° C. 10 ml of a methanol solution of 2.5 g (13.3 mmol) of the 1-fluoro2-oxo-1-cycloheptanecarboxylic acid methyl ester. After stirring at room temperature for 2 hours, the contents were poured into saturated saline, followed by extraction with ethyl acetate. The extract was successively washed with diluted hydrochloric acid, saline, a saturated sodium bicarbonate solution and saline. The ethyl acetate layer was dried over anhydrous sodium sulfate and the solvent was distilled away to obtain 2.3 g of the crude product. The crude product was purified by silica gel column chromatography (developing solvent: hexane/isopropyl alcohol=99/1) to obtain 1.4 g (yield: 55.4%) of 1-fluoro-2-hydroxycycloheptanecarboxylic acid methyl ester in cis form (compound number 134a; 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):

Workup

  1. additionTo the resulting solution was added dropwise in the range of 5° C. to 10° C
  2. additionthe contents were poured into saturated saline
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was successively washed with diluted hydrochloric acid, saline
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away
  7. customto obtain 2.3 g of the crude product
  8. customThe crude product was purified by silica gel column chromatography (developing solvent: hexane/isopropyl alcohol=99/1)

Sources & evidence

ORD record
ord-4b84049a434b4506b722c40f5360798a
Source dataset
uspto-grants-1993_11
Patent number
US05262385

Reaction notes

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