HCID 58238507, compound → HCID 58238506, compound

HRID 1042512Notes

Reaction equation

HRID 1042512 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([C:17]2[C:18]([O:29]C)=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)=[CH2:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:1][O:8][C:9]1[C:14]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:18]=2[OH:29])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 1

HCID 58238507HCID 58238507, compound

Product 1

HCID 58238506HCID 58238506, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5 (0.74 g, 1.58 mmol) in methanol (25 mL) was treated with 20% palladium on activated carbon (50% wet, 0.07 g) and was hydrogenated at 30 psi in a Parr shaker for 2 hr. The catalyst was filtered out and washed with methanol. The filtrate was stripped and the residue was chromatographed on silica (40 g) with 1% ethyl acetate in hexane (3 L). The relevant fractions were stripped and the residue was triturated with ethanol and dried in a vacuum oven at 65° C. to produce pure B1 (0.49 g, 81%).

Workup

  1. filtrationThe catalyst was filtered out
  2. washwashed with methanol
  3. customthe residue was chromatographed on silica (40 g) with 1% ethyl acetate in hexane (3 L)
  4. customthe residue was triturated with ethanol
  5. customdried in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-d66ca4993a3946a6a2a626481dbeacab
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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