3-(Tert-butoxycarbonyl)-2-methyl-6-((2-oxo-2,5-dihydrofuran-3-yl)methyl)benzyl acetate → (S)-3-(tert-butoxycarbonyl)-2-methyl-6-((2-oxo-tetrahydrofuran-3-yl)methyl)benzyl acetate

HRID 2378611Notes

Reaction equation

HRID 2378611 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]([CH2:12][C:13]2[C:14](=[O:18])[O:15][CH2:16][CH:17]=2)=[CH:10][CH:9]=[C:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]=1[CH3:26])(=[O:3])[CH3:2].[H][H]>C(OCC)(=O)C.CO>[C:1]([O:4][CH2:5][C:6]1[C:11]([CH2:12][C@H:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[CH:10][CH:9]=[C:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]=1[CH3:26])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 673195833-(Tert-butoxycarbonyl)-2-methyl-6-((2-oxo-2,5-dihydrofuran-3-yl)methyl)benzyl acetateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67318599(S)-3-(tert-butoxycarbonyl)-2-methyl-6-((2-oxo-tetrahydrofuran-3-yl)methyl)benzyl acetateYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(tert-butoxycarbonyl)-2-methyl-6-((2-oxo-2,5-dihydrofuran-3-yl)methyl)benzyl acetate (280 mg, 0.75 mmol) was dissolved in a mixture of ethyl acetate (10 mL) and methanol (10 mL). A catalytic amount of(−)-1,2-bis((2R,5R)-diethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate was added to the mixture. Reaction vessel was placed on a Parr apparatus and charged with 50 psi of hydrogen gas. Reaction shook at room temperature for 16 hours. A fresh portion of (−)-1,2-bis((2R,5R)-diethylphospholano)benzene(cyclooctadiene)rhodium (I) tetrafluoroborate was added to the mixture. Reaction vessel was charged with 50 psi of hydrogen gas. Reaction shook at room temperature for 24 hours. Reaction mixture was concentrated in vacuo. Residue was passed through a plug of silica gel eluting 80% ethyl acetate-hexanes. Filtrate was concentrated in vacuo. Title compound was obtained as clear colorless oil in 69% yield. MS m/e (M−H)−=376.

Workup

  1. customReaction vessel
  2. customReaction
  3. customReaction vessel
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  5. stirringshook at room temperature for 24 hours
  6. customReaction mixture
  7. concentrationwas concentrated in vacuo
  8. concentrationFiltrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2c921409c59440989ad94fe5aa069985
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Reaction notes

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