HCID 10915366, compound → HCID 15614363, compound

HRID 2191045Notes

Reaction equation

HRID 2191045 reaction equation
[C:1]([O:9][C@@H:10]1[C@H:14]([F:15])[C@@H:13]([CH2:16][O:17]CC2C=CC=CC=2)[O:12][C@@H:11]1[O:25][CH3:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[C:1]([O:9][C@@H:10]1[C@H:14]([F:15])[C@@H:13]([CH2:16][OH:17])[O:12][C@@H:11]1[O:25][CH3:26])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 10915366HCID 10915366, compound

Product 1

HCID 15614363HCID 15614363, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10% formic acid in MeOH (50 mL) was degassed under vacuum for 5 min, and then 20 mL of this solution was added under argon to Pd/C (450 mg). To this suspension, compound 35.10 (450 mg, 1.25 mmol) dissolved in 25 mL of the same solution was added dropwise while stirring. The reaction was monitored by LC-MS. When completed, 50 mL of water was added to the mixture. The catalyst was filtered off and the solvent was removed under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 0-50% EtOAc in Hexane to give compound 35.11 (270 mg, 80% yield).

Workup

  1. customA solution of 10% formic acid in MeOH (50 mL) was degassed under vacuum for 5 min
  2. addition20 mL of this solution was added under argon to Pd/C (450 mg)
  3. additionwas added dropwise
  4. filtrationThe catalyst was filtered off
  5. customthe solvent was removed under reduced pressure
  6. washeluting with 0-50% EtOAc in Hexane

Sources & evidence

ORD record
ord-09ec6d9acc734ce59a8e2caa2834f60a
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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