Sodium borohydride → (1-Phenylcyclopentyl)methanol

To a stirred solution of 1-phenyl-cyclopentanecarbaldehyde (277) (11.5 g, 71.82 mmol) in methanol (150 mL) was added NaBH4 at 0° C. portion-wise and the reaction was stirred at room temperature for 2 h. After completion of the reaction, the reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (20 mL). Subsequently, the methanol was removed, the residue diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL) and the separated organic part was dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 5-10% ethyl acetate in hexane) to get (1-phenyl-cyclopentyl)-methanol] (278) (10 g, 79.0%) as a white solid.

1. customAfter completion of the reaction
2. customthe reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (20 mL)
3. customSubsequently, the methanol was removed
4. additionthe residue diluted with water (100 mL)
5. extractionextracted with ethyl acetate (3×100 mL)
6. customthe separated organic part was dried
7. concentrationconcentrated
8. customThe crude product was purified by Combi-Flash column (eluted at 5-10% ethyl acetate in hexane)

ORD record

ord-fe5ba759481f42868ed98d12c321587e

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045486B2