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

反応式

HRID 413676 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-af394a8d7156425594b34b9f8356597f
出典データセット
uspto-grants-2003_05
特許番号
US06569849B1

関連ノート

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