Toluene → tert-Butyl 4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]-1-piperidinecarboxylate

HRID 412902ノート

反応式

HRID 412902 の反応式
O[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:15]([O:17][C:18]1[CH:27]=[CH:26][C:21]2[N:22]=[C:23]([SH:25])[S:24][C:20]=2[CH:19]=1)[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>C1COCC1>[CH2:15]([O:17][C:18]1[CH:27]=[CH:26][C:21]2[N:22]=[C:23]([S:25][CH:2]3[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]3)[S:24][C:20]=2[CH:19]=1)[CH3:16]

参加物

7

反応物 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 178466040HCID 178466040、化合物

生成物 1

HCID 18538860tert-Butyl 4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]-1-piperidinecarboxylate収率 65%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the mixture of tert-butyl 4-hydroxy-1-piperidinecarboxylate (2 g, 10 mmol), 6-ethoxy-1,3-benzothiazol-2-thiol (2.54 g, 12 mmol), triphenylphosphine (3.9 g, 15 mmol) and THF (60 ml) was dropwise added a solution of 40% diethyl azodicarboxylate in toluene (5.23 g, 15 mmol) under ice cooling over a period of 10 minutes. The mixture was stirred at room tmperature for 20 hours. The reaction mixture was concentrated under reduced pressure, and the concentrate was dissolved in ethyl acetate(50 ml). The organic layer was washed with aqueous solution of 0.5N-sodium hydroxide (30 ml) and saturated aqueous solution of sodium chloride (30 ml), successively, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was subjected to flash column chromatography (silica gel 50 g, ethyl acetate/hexane=1/20 to 1/5), and the desired fraction was concentrated under reduced pressure. To the concentrate was added hexane (10 ml) and the precipitates were collected by filtration to give the titled compound (2.6 g, 6.5 mmol) as white powdery crystals.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe concentrate was dissolved in ethyl acetate(50 ml)
  3. washThe organic layer was washed with aqueous solution of 0.5N-sodium hydroxide (30 ml) and saturated aqueous solution of sodium chloride (30 ml)
  4. dry with materialsuccessively, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationthe desired fraction was concentrated under reduced pressure
  7. additionTo the concentrate was added hexane (10 ml)
  8. filtrationthe precipitates were collected by filtration

出典と根拠

ORDレコード
ord-638f1080ee74428f81b589cd59861f52
出典データセット
uspto-grants-2003_05
特許番号
US06562978B1

反応ノート

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