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

HRID 731250노트

반응식

HRID 731250 반응식
[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]

참가 물질

7

반응물 2

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

생성물 2

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

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-c5a69d51909f49859b405fe289700a0b
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582626B2

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