Sodium borohydride → 1-Benzyl-4-methyl-1,2,3,6-tetrahydropyridine

HRID 2122039노트

반응식

HRID 2122039 반응식
[Cl-].[CH2:2]([N+:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C.O>[CH2:2]([N:9]1[CH2:10][CH:11]=[C:12]([CH3:15])[CH2:13][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 10856996Pyridinium, 4-methyl-1-(phenylmethyl)-, chloride (1:1)

생성물 1

HCID 64215721-Benzyl-4-methyl-1,2,3,6-tetrahydropyridine수율 100%

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

To a stirred solution of the product from Method A (38 grams/0.171 mol) dissolved in 140 mL of 10:1 ethanol/water at 0° C. was added 16 grams (0.427 mol) of sodium borohydride portion-wise over 25 minutes. The resulting mixture stirred for 18 hours at room temperature, at which time, the reaction was quenched upon addition of 100 mL of water. The reaction mixture was filtered, the filter cake washed with water and ethylacetate, and the combined filtrates concentrated under reduced pressure to remove the organics. The residue was diluted with water (100 mL) and extracted 3 times with 150 mL with ethylacetate. The combined ethylacetate extracts were dried over Na2SO4 and concentrated to dryness in vacuo affording 32 grams (100%) of the title compound as a yellow oil. LRMS: 188 (M+1).

후처리

  1. customthe reaction was quenched upon addition of 100 mL of water
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake washed with water and ethylacetate
  4. concentrationthe combined filtrates concentrated under reduced pressure
  5. customto remove the organics
  6. additionThe residue was diluted with water (100 mL)
  7. extractionextracted 3 times with 150 mL with ethylacetate
  8. dry with materialThe combined ethylacetate extracts were dried over Na2SO4
  9. concentrationconcentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-127692d30b9844b88dc66002125de2f2
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696567B2

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