Formaldehyde → (R)-1-(4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acid ethyl ester

HRID 413676

반응식

HRID 413676 반응식
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[C:2]#[CH:3].[CH2:19]([O:21][C:22]([C@@H:24]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]1)=[O:23])[CH3:20].[CH2:30]=O>O1CCOCC1>[CH2:19]([O:21][C:22]([C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][C:3]#[C:2][CH2:1][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][CH2:7][C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]2=3)[CH2:25]1)=[O:23])[CH3:20]

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 185214995-propargyl-10,11-dihydro-5H-dibenzo[b,f]azepine

생성물 1

HCID 53904801(R)-1-(4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acid ethyl ester수율 83%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution containing 5-propargyl-10,11-dihydro-5H-dibenzo[b,f]azepine (2.45 g, 10.5 mmol, prepared similarly as described in U.S. Pat. No. 3,354,178 (1967)), (R)-3-piperidinecarboxylic acid ethyl ester (1.7 g, 10.8 mmol), paraformaldehyde (0.65 g) and a trace of cuprous chloride in dioxane (25 ml) was heated at reflux temperature for 5 h and left standing overnight. The mixture was filtered and the solvent evaporated. The remaining oil was purified by column chromatography on silica gel (40 g) using chloroform as eluent, affording 3.5 g (83%) of (R)-1-(4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acid ethyl ester.

후처리

  1. customprepared similarly
  2. temperatureat reflux temperature for 5 h
  3. waitleft
  4. filtrationThe mixture was filtered
  5. customthe solvent evaporated
  6. customThe remaining oil was purified by column chromatography on silica gel (40 g)

출처 및 근거

ORD 기록
ord-af394a8d7156425594b34b9f8356597f
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06569849B1

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