Hydrazine, 1,1-diphenyl-, hydrochloride (1:1) → 5-Phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester

HRID 269959

反応式

HRID 269959 の反応式
Cl.[C:2]1([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>N1C=CC=CC=1>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26]2[N:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:25]=2[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

参加物

4

反応物 2

HCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

生成物 1

HCID 693140455-Phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester収率 37.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
120 °C

実験手順

A mixture of 1,1-diphenylhydrazine hydrochloride (0.365 g, 1.65 mmol) and 4-oxo-1-piperidinecarboxylic acid tert-butyl ester (0.329 g, 1.65 mmol) in pyridine (3 mL) was heated in a sealed tube at 120° C. with stirring for 3 h. The reaction mixture was subsequently cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4), filtered and evaporated to dryness. The residue was chromatographed (SiO2/hexanes:ethyl acetate, 3:2) to give the title compound (0.214 g, 37%) as a brown oil. 1H NMR (400 MHz, CDCl3) δ 7.51 (m, 2H), 7.40 (m, 1H), 7.35 (m, 2H), 7.26 (m, 2H), 7.14 (m, 2H), 4.72 (s, 2H), 3.78 (s, 2H), 2.71 (s, 2H), 1.51 (s, 9H); LCMS: m/e 349 (M+H)+.

後処理

  1. temperatureThe reaction mixture was subsequently cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was chromatographed (SiO2/hexanes:ethyl acetate, 3:2)

出典と根拠

ORDレコード
ord-8a3392c05c1a4c6b80fc2f6449ae3185
出典データセット
uspto-grants-2008_11
特許番号
US07449476B2

関連ノート

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