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Water → 3-[(R*)-1-((S)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol

HRID 2407331
ノート
印刷プレビュー

反応式

HRID 2407331 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:2]1.C(=O)(O)[O-].[Na+].[CH2:19]([O:26][C:27]1[C:36]2[O:35][CH2:34][C@H:33]([CH2:37]OS(C)(=O)=O)[O:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([O:26][C:27]1[C:36]2[O:35][CH2:34][C@H:33]([CH2:37][N:1]3[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]4[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=4)[CH2:2]3)[O:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 12937952Phenol, 3-(3R)-3-piperidinyl-HCID 86644728Methanesulfonic acid (R)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester

生成物 1

HCID 684875373-[(R*)-1-((S)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol収率 33.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回
HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of hydrochloride salt of (R*)-3-(piperidin-3-yl)-phenol (240 mg, 1.12 mmol) and sodium bicarbonate in N,N-dimethylformamide (3 ml) were stirred at +120° C. under nitrogen atmosphere. To this mixture, a mixture of methanesulfonic acid (R)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester (390 mg, 1.11 mmol) in N,N-dimethylformamide (3 ml) was added, and stirred at +130° C. for 3.5 h. The reaction mixture was cooled down, water (20 ml) and ethyl acetate (15 ml) were added and the layers were separated. Organic phase was recovered and water layer was extracted twice with ethyl acetate. Organic phase and ethyl acetate extracts were combined and washed five times with water and saturated sodium chloride solution. The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified with flash chromatography using heptane and ethyl acetate as eluents to give 160 mg of the title compound.

後処理

  1. additionwas added
  2. stirringstirred at +130° C. for 3.5 h
  3. temperatureThe reaction mixture was cooled down
  4. customthe layers were separated
  5. customOrganic phase was recovered
  6. extractionwater layer was extracted twice with ethyl acetate
  7. washwashed five times with water and saturated sodium chloride solution
  8. dry with materialThe combined organic phase was dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe crude product was purified with flash chromatography

出典と根拠

ORDレコード
ord-7997b99eff2a4b7c9a2f3c1370b173a7
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08809536B2

反応ノート

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