Sodium hydride → 1-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylprop-1-enyl)piperidine

HRID 278220ノート

反応式

HRID 278220 の反応式
[O:1]=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3]P(=O)(OCC)OCC.[H-].[Na+].[CH2:20]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([CH:36]=O)[CH2:32][CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:20]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([CH:36]=[CH:3][C:2](=[O:1])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:32][CH2:31]1)=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 372803Diethyl 2-oxo-2-phenylethylphosphonateHCID 2776272Benzyl 4-formylpiperidine-1-carboxylate

生成物 1

HCID 570744891-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylprop-1-enyl)piperidine収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Diethyl (2-oxo-2-phenylethyl)phosphonate (0.96 mL, 1.1 g, 4.4 mmol) was added in one portion to a stirred suspension of sodium hydride (60% oil dispersion, 158 mg, 3.95 mmol) in THF (20 mL). After 15 min. at rt, the clear solution was cooled in an ice bath and 1-(benzyloxycarbonyl)-4-piperidinecarboxaldehyde (840 mg, 3.40 mmol) was added in THF (1.0 mL) with additional THF (2×1.0 mL) for rinsing. Stirring was continued for a total of 2 h, with slow warming to rt. The mixture was then partitioned between ether (120 mL) and 2.5 N aq. NaOH (60 mL). The organic layer was washed with saturated aq. brine (60 mL), dried (sodium sulfate), decanted, and evaporated. The crude product was purified by FC, eluting with 15-20% ethyl acetate in hexane, to give 0.95 g of the title compound as a colorless syrup.

後処理

  1. temperaturethe clear solution was cooled in an ice bath
  2. washfor rinsing
  3. customwas continued for a total of 2 h
  4. customThe mixture was then partitioned between ether (120 mL) and 2.5 N aq. NaOH (60 mL)
  5. washThe organic layer was washed with saturated aq. brine (60 mL)
  6. dry with materialdried (sodium sulfate)
  7. customdecanted
  8. customevaporated
  9. customThe crude product was purified by FC
  10. washeluting with 15-20% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-d8f24cbc4070496f867a1929c49be4c8
出典データセット
uspto-grants-2002_03
特許番号
US06358979B1

反応ノート

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