Piperidin-4-ol → 1-(Cyclopropylmethyl)piperidin-4-ol

HRID 1821982

반응식

HRID 1821982 반응식
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[OH:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1>C1COCC1.C(OC(=O)C)C>[CH:5]1([CH2:4][N:10]2[CH2:11][CH2:12][CH:7]([OH:6])[CH2:8][CH2:9]2)[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 79341Piperidin-4-olHCID 81503Bromomethylcyclopropane

생성물 1

HCID 214287521-(Cyclopropylmethyl)piperidin-4-ol수율 47%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Add bromomethylcyclopropane (2.025 g, 15 mmol) to a solution of 4-hydroxypiperidine (3.035 g, 30 mmol) in THF (10 mL) and stir the mixture overnight. Dilute the mixture with ethylacetate, wash with saturated NaHCO3 solution, dry over Na2SO4, filter and concentrate to give a residue. Chromatography (silica gel, eluting with 8% 2M NH3-methanol in CH2Cl2) provides 1.087 g (47%) of the title compound: mass spectrum (ion spray): m/z=156.2 (M+1); 1H NMR (CDCl3, ppm): 3.60 (m, 1H), 2.81 (m, 2H), 2.16 (d, 1H), 2.10 (m, 3H), 1.84 (m, 2H), 1.53 (m, 3H), 0.79 (m, 1H), 0.44 (m, 2H), 0.00 (m, 2H).

후처리

  1. washwash with saturated NaHCO3 solution
  2. dry with materialdry over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customto give a residue
  6. washChromatography (silica gel, eluting with 8% 2M NH3-methanol in CH2Cl2)

출처 및 근거

ORD 기록
ord-477683910d6f4a09a72aa1c87f311dca
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608629B2

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