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

HRID 1821982

反応式

HRID 1821982 の反応式
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

参加物

5

反応物 2

HCID 79341Piperidin-4-olHCID 81503Bromomethylcyclopropane

生成物 1

HCID 214287521-(Cyclopropylmethyl)piperidin-4-ol収率 47%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-477683910d6f4a09a72aa1c87f311dca
出典データセット
uspto-grants-2009_10
特許番号
US07608629B2

関連ノート

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