Methanol → (R)-1-(3-Tert-butyloxycarbonylphenyl)ethanol

HRID 2300770노트

반응식

HRID 2300770 반응식
[C:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])(=[O:3])[CH3:2].CO>C(Cl)Cl>[C:10]([O:9][C:7]([C:6]1[CH:5]=[C:4]([C@H:1]([OH:3])[CH3:2])[CH:16]=[CH:15][CH:14]=1)=[O:8])([CH3:13])([CH3:11])[CH3:12]

참가 물질

4

반응물 2

HCID 887MethanolHCID 46941403tert-Butyl 3-acetylbenzoate

생성물 1

HCID 69964056(R)-1-(3-Tert-butyloxycarbonylphenyl)ethanol수율 92.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

In a dry flask under nitrogen, (S)-oxazaborolidine (4.81 mmol) was dissolved in dry CH2Cl2 (12 mL). This solution was maintained between −20° C. and −25° C. as a solution of tert-butyl (3-acetyl)benzoate (4.20 mmol) in dry CH2Cl2 (12 mL) was added dropwise over 20 minutes. The reaction mixture was then allowed to warm to room temperature for 45 minutes. This mixture was then cooled to −78° C. and methanol (20 mL) added dropwise. The mixture was allowed to warm to room temperature. Solvent was removed under reduced pressure then the residue dissolved in methanol and concentrated under reduced pressure twice more. The dried residue was purified by silica gel chromatography in 10-30% ethyl acetate/hexanes to yield 865 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.00 (m, 1H); 7.92 (m, 1H); 7.58 (d, J=7.5 Hz, 1H); 7.42 (t, J=7.7 Hz, 1H); 4.98 (m, 1H); 1.62 (s, 9H); 1.54 (d, J=6.4 Hz, 3H).

후처리

  1. additionwas added dropwise over 20 minutes
  2. temperatureThis mixture was then cooled to −78° C.
  3. temperatureto warm to room temperature
  4. customSolvent was removed under reduced pressure
  5. dissolutionthe residue dissolved in methanol
  6. concentrationconcentrated under reduced pressure twice more
  7. customThe dried residue was purified by silica gel chromatography in 10-30% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-c3f89156c3ff47baa367b34071f557d1
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498165B1

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