HCID 67247225, compound → HCID 68267476, compound

HRID 1027575Notes

Reaction equation

HRID 1027575 reaction equation
C([O:8][CH2:9][CH:10]1[CH2:14][S:13](=[O:16])(=[O:15])[N:12]([CH2:17][CH3:18])[CH2:11]1)C1C=CC=CC=1>CO.[Pd]>[CH2:17]([N:12]1[CH2:11][CH:10]([CH2:9][OH:8])[CH2:14][S:13]1(=[O:16])=[O:15])[CH3:18]

Participants

4

Reactant 1

HCID 67247225HCID 67247225, compound

Product 1

HCID 68267476HCID 68267476, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-Benzyloxymethyl-2-ethyl-isothiazolidine 1,1-dioxide (254 mg) and Pd/C (108 mg, 0.1 equiv) in methanol was purged with H2 and left to stir under an H2 atmosphere for 24 h. As LCMS indicated completion, the reaction mixture was filtered through a pad of silica (rinsing with MeOH). The filtrate was evaporated and 162 mg of the expected alcohol were obtained. It was pure enough to be used as such in the next step. LCMS (Method E) 0.25 min, M+H 170. 1H-NMR (CDCl3, 400 MHz): 3.8-3.70 (m, 2H), 3.39-3.25 (m, 2H), 3.20-3.01 (m, 4H), 2.94-2.78 (m, 1H), 1.24 (t, 3H).

Workup

  1. customwas purged with H2
  2. waitleft
  3. filtrationthe reaction mixture was filtered through a pad of silica (rinsing with MeOH)
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b861f6bf97394cadb8cbb9bc8d62836b
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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