Benzyl Bromide → HCID 131737023, compound

Temperature

40 °C

Pd/C (10%, 3 g) was added to a solution of 3,4-dihydro-2H-pyran-5-carboxylic acid (7.0 g, 55 mmol) in MeOH (100 mL). The suspension was stirred under hydrogen atmosphere (100 psi) at 40° C. for 10 h. The catalyst was filtered off and washed with MeOH (50 mL). The filtrate and washings were combined and concentrated to dryness to afford crude product. The crude product was dissolved in acetonitrile (200 mL) and benzyl bromide (9.9 g, 58 mmol) and K2CO3 (19.0 g, 138 mmol) were added. The resulting suspension was heated at 50-60° C. for 4 h and then cooled to ambient temperature. The mixture was filtered and the filtration cake was washed with acetonitrile (50 mL). The filtrate and washings were combined and concentrated to dryness. The residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=20:1) to afford a mixture (7.1 g) of (S)-benzyl tetrahydro-2H-pyran-3-carboxylate and (R)-benzyl tetrahydro-2H-pyran-3-carboxylate, which was separated by chiral prep-HPLC to afford (S)-benzyl tetrahydro-2H-pyran-3-carboxylate (2.1 g, 17% yield) and (R)-benzyl tetrahydro-2H-pyran-3-carboxylate (2.0 g, 16% yield), respectively.

1. filtrationThe catalyst was filtered off
2. washwashed with MeOH (50 mL)
3. concentrationconcentrated to dryness
4. customto afford crude product
5. temperatureThe resulting suspension was heated at 50-60° C. for 4 h
6. temperaturecooled to ambient temperature
7. filtrationThe mixture was filtered
8. washthe filtration cake was washed with acetonitrile (50 mL)
9. concentrationconcentrated to dryness
10. customThe residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=20:1)

ORD record

ord-a67f8587c41d4a39b671c20338bf93d7

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434761B2