Water → benzyl((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylpent-4-en-1-yl)carbamate

HRID 2046659Notes

Reaction equation

HRID 2046659 reaction equation
[OH:1][CH:2]([CH2:16][CH:17]=[CH2:18])[C@@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].N1C(C)=CC=CC=1C.FC(F)(F)S(O)(=O)=O.[C:35]([SiH:39]([CH3:41])[CH3:40])([CH3:38])([CH3:37])[CH3:36].O>O1CCCC1>[CH2:8]([O:7][C:6](=[O:15])[NH:5][C@@H:3]([CH3:4])[CH:2]([O:1][Si:39]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:41])[CH3:40])[CH2:16][CH:17]=[CH2:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 14481674benzyl [(1S)-2-hydroxy-1-methylpent-4-en-1-yl]carbamateHCID 131728534Tert-butyldimethylsilane trifluoromethanesulfonate

Product 1

HCID 59370536benzyl((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylpent-4-en-1-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (30 mL) of benzyl [(1S)-1-methyl-2-oxoethyl]carbamate (3.0 g) in tetrahydrofuran was added 1.0 mol/L solution (28.8 mL) of allylmagnesium bromide in tetrahydrofuran under ice-cooling, and the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=9:1→1:1) to give benzyl [(1S)-2-hydroxy-1-methylpent-4-en-1-yl]carbamate as a colorless oil. To a solution (10 mL) of the obtained benzyl [(1S)-2-hydroxy-1-methylpent-4-en-1-yl]carbamate in tetrahydrofuran were added 2,6-lutidine (0.629 mL) and tert-butyldimethylsilane trifluoromethanesulfonate (0.91 mL) and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=9:1→2:1) to give the title compound as a colorless oil (yield: 610 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=9:1→2:1)

Sources & evidence

ORD record
ord-bc58e62b665f4d68aa83288f27aec47f
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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