Ethanol → (S)-ethyl 1-(2-thiopheneacetyl)-3-hydroxymethylpiperidine

HRID 432826ノート

反応式

HRID 432826 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([O:17]CC)=O)[CH2:10]1)=[O:8].[BH4-].[Na+].[CH2:22](O)[CH3:23]>ClCCl>[CH2:22]([C@H:10]1[CH:11]([CH2:15][OH:17])[CH2:12][CH2:13][CH2:14][N:9]1[C:7](=[O:8])[CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH3:23]

参加物

5

反応物 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 9838651(S)-ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxylate

生成物 1

HCID 86759306(S)-ethyl 1-(2-thiopheneacetyl)-3-hydroxymethylpiperidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(S)-ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxylate (1.053 g; 3.75 mmol) was dissolved in absolute ethanol (40 ml). Sodium borohydride (2 g; 52.9 mmol) was added and this mixture was heated to reflux. The mixture was allowed to reflux for 1 hour and was then cooled to ambient temperature, diluted with dichloromethane and carefully quenched and washed with 1 N HCl. The dichloromethane was separated, washed with saturated sodium chloride solution, dried with anhydrous potassium carbonate, and evaporated under reduced pressure at ambient temperature. The crude product was purified by chromatography on silica eluting with 100% ethyl acetate, giving (S)-ethyl 1-(2-thiopheneacetyl)-3-hydroxymethylpiperidine (715.5 mg) as a thick colorless oil. MS m/z (positive ion) 501 (dimer+Na+; 50), 488 (30), 262 (M+Na+; 75), 249 (50), 240 (MH+; 80), 102 (Et3NH+; 100).

後処理

  1. temperaturethis mixture was heated to reflux
  2. temperatureto reflux for 1 hour
  3. customcarefully quenched
  4. washwashed with 1 N HCl
  5. customThe dichloromethane was separated
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried with anhydrous potassium carbonate
  8. customevaporated under reduced pressure at ambient temperature
  9. customThe crude product was purified by chromatography on silica eluting with 100% ethyl acetate

出典と根拠

ORDレコード
ord-2bed498020bf4802b53494a2b8039064
出典データセット
uspto-grants-2003_12
特許番号
US06664271B1

反応ノート

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