HCID 67105696, compound → HCID 86652833, compound

HRID 1042517Notes

Reaction equation

C([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]([C:21]1[C:22]([O:33][CH3:34])=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1)=[CH2:20])C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[C:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:19]([C:21]2[C:22]([O:33][CH3:34])=[C:23]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:24]=[CH:25][CH:26]=2)[CH3:20])[C:9]=1[OH:8])([CH3:16])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 12 (1.05 g, 2.34 mmol) in methanol (30 mL) and ethyl acetate (60 mL) was treated with 20% palladium on activated carbon (50% wet, 0.10 g) and was hydrogenated at 30 psi in a Parr shaker for 16 hr. The catalyst was filtered out and washed with ethyl acetate. The solvent was removed in a rotary evaporator and the crude product was purified by chromatography on silica (80 g) with 1% ethyl acetate in hexane (3 L). The relevant fractions were stripped and the residue was taken up in ethanol (10 mL) and stirred at 65° C. for 30 min. The resulting slurry was allowed to cool overnight. The crystals were collected by filtration, washed with cold ethanol and dried in a vacuum oven at 65° C. to produce pure B3 (0.29 g, 35%).

Workup

filtrationThe catalyst was filtered out
washwashed with ethyl acetate
customThe solvent was removed in a rotary evaporator
customthe crude product was purified by chromatography on silica (80 g) with 1% ethyl acetate in hexane (3 L)
temperatureto cool overnight
filtrationThe crystals were collected by filtration
washwashed with cold ethanol
customdried in a vacuum oven at 65° C.

Sources & evidence

ORD record: ord-07ac556781f745aea2725804003baabe
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557936B2

Reaction notes

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