HCID 58869132, compound → HCID 58869192, compound

HRID 2355201Notes

Reaction equation

HRID 2355201 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([CH2:9][CH:10]1[CH2:19][C:18](=[O:20])[C:17]2[C:12](=[CH:13][C:14]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:15][CH:16]=2)[O:11]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:30])[N:7]([CH2:9][CH:10]1[CH2:19][CH:18]([OH:20])[C:17]2[C:12](=[CH:13][C:14]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:15][CH:16]=2)[O:11]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58869132HCID 58869132, compound

Product 1

HCID 58869192HCID 58869192, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (7-benzenesulfonyl-4-oxo-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (216 mg, 0.5 mmol) in MeOH (40 mL) was added Pd/C (10%, 20 mg) and the mixture was stirred under balloon pressure of H2 overnight. The reaction was filtered through a celite pad and the filtrate was concentrated in vacuo. The residue was purified via flash chromatography (DCM/MeOH, 99/1) to give (7-benzenesulfonyl-4-hydroxy-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (159 mg, 74% yield).

Workup

  1. filtrationThe reaction was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified via flash chromatography (DCM/MeOH, 99/1)

Sources & evidence

ORD record
ord-964cc106f8f341fda528b47ea00fc5c4
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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