Borane;tetrahydrofuran → HCID 66886100, compound

HRID 2246933Notes

Reaction equation

HRID 2246933 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][C@@H:11]([CH2:25][OH:26])[N:12]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:13][CH:14]=2)=[CH:5][CH:4]=1.B.[O:28]1CCCC1>O1CCCC1>[OH:26][CH2:25][C@H:11]1[N:12]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH2:13][C@H:14]([OH:28])[C@@H:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68454482HCID 68454482, compound

Product 1

HCID 66886100HCID 66886100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 108.1 g of [(S)-4-(4-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-methanol in 1000 ml of tetrahydrofuran are added 504 ml of a solution of borane-tetrahydrofuran (1M) at room temperature. The reaction mixture is heated to 40° C. for 2-6 hours, cooled to room temperature, and quenched by the addition of 150 ml of 2N sodium hydroxide solution and 150 ml of 30% hydrogen peroxide solution. The organic phase is separated, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a white solid. Rf=0.19 (EtOAc-heptane 1:1); Rt=3.67.

Workup

  1. temperaturecooled to room temperature
  2. customquenched by the addition of 150 ml of 2N sodium hydroxide solution and 150 ml of 30% hydrogen peroxide solution
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-9fb59843a2ce408bac01d13bcff4fcf3
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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