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

HRID 415352

反応式

HRID 415352 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e3fafe93775640ec8fbc1ed11a1b790a
出典データセット
uspto-grants-2012_01
特許番号
US08088780B2

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