HCID 67103683, compound → HCID 86652860, compound

HRID 45449Notes

Reaction equation

HRID 45449 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]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH2:26])[CH:20]=1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[C:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH3:26])[CH:20]=2)[C:9]=1[OH:8])([CH3:16])([CH3:17])[CH3:18]

Participants

5

Reactant 1

HCID 67103683HCID 67103683, compound

Product 1

HCID 86652860HCID 86652860, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 12 (0.13 g, 0.31 mmol) in methanol (10 mL) and ethyl acetate (30 mL) was treated with 20% palladium on activated carbon (50% wet, 0.05 g) and was hydrogenated at 10 psi in a Parr shaker for 2 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 (25 g) with 5% ethyl acetate in hexane (3 L). Pure B1 (0.08 g, 80%) was isolated.

Workup

  1. filtrationThe catalyst was filtered out
  2. washwashed with ethyl acetate
  3. customThe solvent was removed in a rotary evaporator
  4. customthe crude product was purified by chromatography on silica (25 g) with 5% ethyl acetate in hexane (3 L)

Sources & evidence

ORD record
ord-17354b6522cb4761a04dab00061f4edb
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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