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

HRID 415352

Reaction equation

HRID 415352 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e3fafe93775640ec8fbc1ed11a1b790a
Source dataset
uspto-grants-2012_01
Patent number
US08088780B2

Linked notes

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