HCID 58869132, compound → HCID 58869152, compound

HRID 2355202Notes

Reaction equation

HRID 2355202 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([CH2:9][CH:10]1[CH2:19][C:18](=O)[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.Cl.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:30])[N:7]([CH2:9][CH:10]1[CH2:19][CH2:18][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

5

Reactant 1

HCID 58869132HCID 58869132, compound

Product 1

HCID 58869152HCID 58869152, compoundYield 98.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (7-benzenesulfonyl-4-oxo-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (155 mg, 0.359 mmol) in MeOH (50 mL) were added Pd(OH)2 (10 mg) and HCl (concentrated, 5 drops) the mixture was shaken into a Parr apparatus under H2 atmosphere (50 PSI) for 3 hours. The reaction was filtered through a celite pad and the filtrate was neutralized with Na2CO3. The mixture was filtered and the filtrate was concentrated in vacuo. The residue purified via flash chromatography (DCM/MeOH, 99/1) to give (7-benzenesulfonyl-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (147 mg, 98% yield) as a clear glass.

Workup

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

Sources & evidence

ORD record
ord-004ad1a1de0c464aaf3269d42d302118
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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