Lithium borohydride → (8-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol

HRID 1802528Notes

Reaction equation

HRID 1802528 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([C:20](OCC)=[O:21])[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+]>O1CCCC1>[CH2:1]([O:8][CH2:9][C:10]1([CH2:20][OH:21])[CH2:19][CH2:18][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58399380Ethyl 8-(benzyloxymethyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate

Product 1

HCID 58399365(8-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanolYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 8-(benzyloxymethyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate (Reference Example 84) (279 mg, 0.834 mmol) in tetrahydrofuran (4.2 mL), lithium borohydride (91.0 mg, 4.17 mmol) was added with stirring under ice-cooling, and the obtained solution was stirred at 70° C. for 4 hours. The reaction was quenched by adding saturated aqueous ammonium chloride solution to the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (183 mg, 0.625 mmol, 75%) as a colorless oily compound.

Workup

  1. temperaturecooling
  2. stirringthe obtained solution was stirred at 70° C. for 4 hours
  3. customThe reaction was quenched
  4. additionby adding saturated aqueous ammonium chloride solution to the reaction solution
  5. extractionthe resulting solution was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-738a9960a5cc414b832831943a8c490e
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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