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

반응식

HRID 269959 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
120 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-8a3392c05c1a4c6b80fc2f6449ae3185
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449476B2

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