Methyl Ethyl Ketone → (R)-1-(4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-benzyl)-3-piperidinecarboxylic acid ethyl ester

HRID 413675

反応式

HRID 413675 の反応式
[I-].[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)=[O:6])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20](=O)[CH2:21][CH3:22]>CCOCC.O>[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH2:19][C:20]2[CH:22]=[CH:21][C:20]([CH:19]3[C:21]4[CH:22]=[CH:5][CH:7]=[CH:8][C:20]=4[CH2:19][CH2:22][C:21]4[CH:10]=[CH:11][CH:12]=[CH:19][C:20]3=4)=[CH:22][CH:21]=2)[CH2:8]1)=[O:6])[CH3:3]

参加物

7

反応物 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 185582ethyl (3R)-piperidine-3-carboxylate

生成物 1

HCID 53835769(R)-1-(4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-benzyl)-3-piperidinecarboxylic acid ethyl ester収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
50 °C

実験手順

A mixture of the above iodide (1.80 g, 0.0044 mol), (R)-3-piperidinecarboxylic acid ethyl ester (0.69 g, 0.0044 mol) and anhydrous potassium carbonate (1.82 g, 0.0132 mol) in 2-butanone (30 ml) was heated to 50° C. for 6 h. After cooling, the mixture was diluted with ether (50 ml) and water (50 ml) and the phases were separated. The organic phase was washed with water (30 ml) and dried (MgSO4). The solvent was evaporated in vacuo and the oily residue (2.1 g) was purified by gradient column chromatography on silica gel (40 g) using benzene and ethyl acetate as eluents. The benzene/ethyl acetate (9:1) fraction afforded 1.50 g (77%) of (R)-1-(4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-benzyl)-3-piperidinecarboxylic acid ethyl ester.

後処理

  1. temperatureAfter cooling
  2. customthe phases were separated
  3. washThe organic phase was washed with water (30 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated in vacuo
  6. customthe oily residue (2.1 g) was purified by gradient column chromatography on silica gel (40 g)

出典と根拠

ORDレコード
ord-58df006fae444ce5a99798597a2d0096
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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