HCID 25133899, compound → HCID 25129450, compound

HRID 1889132Notes

Reaction equation

HRID 1889132 reaction equation
C([O:8][CH:9]1[CH2:18][O:17][CH2:16][CH2:15][S:14](=[O:20])(=[O:19])[CH2:13][CH2:12][O:11][CH2:10]1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH:9]1([OH:8])[CH2:10][O:11][CH2:12][CH2:13][S:14](=[O:20])(=[O:19])[CH2:15][CH2:16][O:17][CH2:18]1

Participants

4

Reactant 1

HCID 25133899HCID 25133899, compound

Product 1

HCID 25129450HCID 25129450, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 22 (25 mg, 0.083 mmol) and a catalytic amount of 10% Pd/C in EtOAc (3 mL) was stirred at 23° C. under a hydrogen atmosphere. After 48 h the catalyst was filtered off and the filtrate was evaporated to afford 16 mg (92%) of 81 as a colorless oil: 1H NMR (CDCl3) δ 4.08-3.95 (m, 4H), 3.67 (dd, J=4.2, 9.9 Hz, 2H), 3.61-3.59 (m, 1H), 3.51 (dd, J=5.7, 9.9 Hz, 2H), 3.38-3.23 (m, 4H); 13C NMR (CDCl3) δ 69.0, 68.3, 64.5, 52.6.

Workup

  1. filtrationAfter 48 h the catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9663b38ec9924f448551c93f62091b05
Source dataset
uspto-grants-2013_08
Patent number
US08501961B2

Reaction notes

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