Sodium cyanoborohydride → 2-(2-Dimethylamino-ethylideneamino)-cyclopentanecarboxylic acid ethyl ester

HRID 731250ノート

反応式

HRID 731250 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[NH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[O:5])[CH3:2].C([BH3-])#N.[Na+]>C(O)C.C(O)(=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[NH:11][CH2:12][CH2:13][N:14]([CH3:15])[CH3:16])=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[N:11]=[CH:12][CH2:13][N:14]([CH3:15])[CH3:16])=[O:5])[CH3:2]

参加物

7

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 576711902-(2-Dimethylamino-ethylamino)-cyclopent-1-enecarboxylic acid ethyl ester

生成物 2

HCID 576712582-(2-Dimethylamino-ethylamino)-cyclopentanecarboxylic acid ethyl esterHCID 690599592-(2-Dimethylamino-ethylideneamino)-cyclopentanecarboxylic acid ethyl ester収率 167.4%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A solution of 2-(2-dimethylamino-ethylamino)-cyclopent-1-enecarboxylic acid ethyl ester (2.18 g, 9.63 mmol) in ethanol (100 mL) was treated with glacial acetic acid (10 drops), sodium cyanoborohydride (1.21 g, 19.26 mmol) and stirred for 16 h at 50° C. The reaction was diluted with ethyl acetate (100 mL) and washed twice with saturated aqueous sodium bicarbonate solution (100 mL). The organic layer was dried over sodium sulfate, filtered, concentrated in vacuo to afford the desired product, 2-(2-dimethylamino-ethylideneamino)-cyclopentanecarboxylic acid ethyl ester (1.84 g, 8.06 mmol, 83.7%), as a light yellow oil. LC-MS (ESI) calcd for C12H24N2O2 228.18, found 229.3 [M+H+].

後処理

  1. washwashed twice with saturated aqueous sodium bicarbonate solution (100 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c5a69d51909f49859b405fe289700a0b
出典データセット
uspto-grants-2009_09
特許番号
US07582626B2

反応ノート

読み込み中…