HCID 86706786, compound → HCID 60164156, compound

Temperature

0 °C

A solution of (6-hydroxy-1-benzofuran-3-yl)acetic acid (1R)-1-phenylethylamine salt (8.16 g) and dichloro[(+)-1,2-bis((2R,5R)-2,5-diisopropylphosphorano)benzene]ruthenium (II)—N,N-dimethylformamide complex (1.3 mg) in dehydrated methanol (50 ml) was stirred at 35° C. for 26 hr under a hydrogen atmosphere (1.1 MPa). After concentration, the residue was dissolved in a mixed solvent of methanol (25.0 mL)-water (3.7 mL) at around 55° C. After adding toluene (225 mL) at the same temperature, the mixture was stirred at 25° C. for 20 hr and at 0° C. for 1 hr. The precipitated crystals were collected by filtration, washed with toluene (25 mL), and dried at 50° C. under reduced pressure to give a crude product (6.65 g). The crude product was subjected to a similar recrystallization method using a mixed solvent of methanol (20.0 mL)-water (3.0 mL) and diisopropyl ether (180 mL) to give a crude product (6.16 g). The crude product was subjected to a similar recrystallization method using a mixed solvent of methanol (18.5 mL)-water (2.8 mL) and diisopropyl ether (166 mL) to give the title compound (5.81 g) as white crystals. 99.7% de.

1. concentrationAfter concentration
2. dissolutionthe residue was dissolved in a mixed solvent of methanol (25.0 mL)-water (3.7 mL) at around 55° C
3. additionAfter adding toluene (225 mL) at the same temperature
4. filtrationThe precipitated crystals were collected by filtration
5. washwashed with toluene (25 mL)
6. customdried at 50° C. under reduced pressure
7. customto give a crude product (6.65 g)
8. customThe crude product was subjected to a similar recrystallization method
9. customto give a crude product (6.16 g)
10. customThe crude product was subjected to a similar recrystallization method

ORD record

ord-564a5d6955054bcfa4794ceb23fe3f38

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952185B2