HCID 10991787, compound → (S)-5-(((tert-Butyldiphenylsilyl)oxy)methyl)dihydrofuran-2(3H)-one

HRID 60765Notes

Reaction equation

HRID 60765 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]1[CH:24]=[CH:23][C:22](=[O:25])[O:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[Si:1]([O:18][CH2:19][C@H:20]1[O:21][C:22](=[O:25])[CH2:23][CH2:24]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 10991787HCID 10991787, compound2×

Product 1

HCID 11002733(S)-5-(((tert-Butyldiphenylsilyl)oxy)methyl)dihydrofuran-2(3H)-oneYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (25)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-2H-furan-5-one (compound 40c, 2.8 g, 8.0 mmol) in EtOAc (40 mL) was stirred with 10% palladium on carbon (280 mg) under hydrogen atmosphere overnight. The resulting mixture was filtered and the filtrate was concentrated in vacuo to afford 2.7 g of (5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2-one (compound 40d) as a viscous oil. MS obsd. (ESI+) [(M+H)+]: 355.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a28cb4b042be49d2bf44552651cf3372
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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