Ethyl iodoacetate → (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-ethoxy-2-oxoethoxy)ethyl)piperidine-1-carboxylate

HRID 451912

反応式

HRID 451912 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)([O:10][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:9])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 59201475(R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-hydroxyethyl)piperidine-1-carboxylate

生成物 1

HCID 59201464(R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-ethoxy-2-oxoethoxy)ethyl)piperidine-1-carboxylate収率 14.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

A mixture of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-hydroxyethyl)piperidine-1-carboxylate (0.4395 g, 1.29 mmol), 60% NaH (1.320 g, 33 mmol), and ethyl iodoacetate (5.237 g, 24.5 mmol) in THF (20 mL) was heated at 90° C. for 18 h and then cooled to rt. The reaction mixture was then quenched with saturated brine and extracted with ethyl acetate (3×), dried over Na2SO4. After the solvent was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC to afford 0.0775 g (14%) of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-ethoxy-2-oxoethoxy)ethyl)piperidine-1-carboxylate. MS ESI +ve m/z 450 (M+Na).

後処理

  1. temperaturecooled to rt
  2. customThe reaction mixture was then quenched with saturated brine
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried over Na2SO4
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe crude product was purified by reversed-phase HPLC

出典と根拠

ORDレコード
ord-e133ecb36842431cb226d0c1e34b4a8e
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

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