Sodium hydride → Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate

HRID 564556

反応式

HRID 564556 の反応式
[Br-].[Br:2][C:3]1[CH:4]=[C:5]([CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].O=[C:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1>CN(C=O)C.CCOCC>[Br:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:32]2[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]2)[CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 19034144[(3-Bromophenyl)methyl](triphenyl)phosphanium bromide

生成物 1

HCID 57813409Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate収率 28.6%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

To [(3-bromophenyl)methyl](triphenyl)phosphonium bromide (1.13 mg, 2.2 mmol) in DMF (4 mL) was added NaH (52.8 mg, 2.2 mmol) after which the mixture was stirred at RT for 5 min before 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (400 mg, 2.0 mmol) was added. This mixture was stirred at RT for 1 h. The resultant mixture was diluted with Et2O (25 mL), washed with H2O (12+2×8 mL), brine (8 mL), dried over NaSO4, and filtered. The filtrate was concentrated and purified with CombiFlash chromatograph to afford the title compound (0.2014 g, 28%). LC-MS m/z 352 (M+H)+.

後処理

  1. additionwas added
  2. washwashed with H2O (12+2×8 mL), brine (8 mL)
  3. dry with materialdried over NaSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified with CombiFlash chromatograph

出典と根拠

ORDレコード
ord-961cfee4a57842e1b32e1a502718ea82
出典データセット
uspto-grants-2011_11
特許番号
US08067408B2

関連ノート

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