Methanol → [4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-methanol

HRID 1959604노트

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HRID 1959604 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=C)[C:3]=1[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[BH4-].[Na+].C[OH:21]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:21])[C:3]=1[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 441905854-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridine

생성물 1

HCID 44191034[4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-methanol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-50 °C

실험 절차

4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridine (300 mg. 1.29 mmol) was dissolved in DCM (36 mL) and cooled to −50° C. A gentle flow of ozone was bubbled through the reaction mixture until the colour of the solution changed to slight blue. NaBH4 (486 mg. 12.9 mmol) dissolved in MeOH (15 mL) was added and the reaction was allowed to warm to RT over a period of 1 h. The solvents were removed in vacuo and the residue pardoned between water (20 mL) and EtOAc (20 mL) extracted with EtOAc (3×20 mL). The combined organic fractions were washed with brine and dried over Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with DCM/MeOH 40:1→20:1) to give the title compound. MS (m/z): 238.0 [M+H+].

후처리

  1. customA gentle flow of ozone was bubbled through the reaction mixture until the colour of the solution
  2. additionwas added
  3. temperatureto warm to RT over a period of 1 h
  4. customThe solvents were removed in vacuo
  5. extractionextracted with EtOAc (3×20 mL)
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography on silica gel (elution with DCM/MeOH 40:1→20:1)

출처 및 근거

ORD 기록
ord-5c3f58b4766547e6866a9d01f809a2c3
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410134B2

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