Ethyl Acetate → ((1S,2S)-2-((Benzyloxy)methyl)cyclopropyl)methanol

Lithium aluminium hydride (0.238 g, 6.27 mmol) was added to a solution of methyl (1S,2S)-2-((benzyloxy)methyl)cyclopropanecarboxylate (1.38 g, 6.27 mmol) in THF (15 mL) at 0° C. The reaction mixture was stirred at room temperature for 15 hr, and ethyl acetate (5 mL) and saturated aqueous potassium sodium tartrate solution (25 mL) were added thereto at 0° C. The mixture was stirred at room temperature for 30 min, water (60 mL) was added thereto, and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 37→58% ethyl acetate/hexane) to give ((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)methanol (1.01 g, 5.25 mmol, 84%) as a colorless oil.

1. customat 0° C
2. stirringThe mixture was stirred at room temperature for 30 min
3. extractionthe mixture was extracted with ethyl acetate (×3)
4. washThe organic layer was washed with water and brine
5. dry with materialdried over magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 37→58% ethyl acetate/hexane)

ORD record

ord-d01d99594afd4f3483a4c5994596ff43

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365520B2