Trimethyl borate → (1R)-1-(3-methanesulfonylphenyl)ethan-1-ol

HRID 415352

반응식

HRID 415352 반응식
B(OC)(OC)OC.C1(C(C2C=CC=CC=2)([C@H]2CCCN2)O)C=CC=CC=1.[CH3:27][S:28]([C:31]1[CH:32]=[C:33]([C:37](=[O:39])[CH3:38])[CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29]>C1COCC1>[CH3:27][S:28]([C:31]1[CH:32]=[C:33]([C@H:37]([OH:39])[CH3:38])[CH:34]=[CH:35][CH:36]=1)(=[O:29])=[O:30]

참가 물질

5

반응물 3

HCID 8470Trimethyl borateHCID 70453712-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (R)-HCID 597414371-(3-Methanesulfonylphenyl)ethan-1-one

생성물 1

HCID 66622848(1R)-1-(3-methanesulfonylphenyl)ethan-1-ol수율 81.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

B(OMe)3 (62 μL, 0.55 mmol) was added to (R)-(+)-α,α-diphenyl-2-pyrrolidinemethanol in THF (5 mL) followed by BH3.Me3S (2M in THF, 1.23 mL, 2.54 mmol). The mixture was stirred for 1 h before 1-[3-(methylsulfonyl)phenyl]ethanone (458 mg, 2.31 mmol) in THF (5 mL) was added over 1.5 h. The resulting mixture was stirred overnight and then quenched with 1M HCl (2 mL). The mixture was concentrated and the crude product was purified by flash column chromatography (CH2Cl2/MeOH 50:1) to give the title compound (378 mg, 18% yield).

후처리

  1. additionwas added over 1.5 h
  2. customquenched with 1M HCl (2 mL)
  3. concentrationThe mixture was concentrated
  4. customthe crude product was purified by flash column chromatography (CH2Cl2/MeOH 50:1)

출처 및 근거

ORD 기록
ord-e3fafe93775640ec8fbc1ed11a1b790a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088780B2

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