Ethyl 2-oxocyclopentanecarboxylate → 2-(Cyclobutylmethyl-amino)-cyclopentanecarboxylic acid ethyl ester

HRID 731356노트

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HRID 731356 반응식
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=O)=[O:5])[CH3:2].Cl.[CH:13]1([CH2:17][NH2:18])[CH2:16][CH2:15][CH2:14]1.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[NH:18][CH2:17][CH:13]1[CH2:16][CH2:15][CH2:14]1)=[O:5])[CH3:2]

참가 물질

8

반응물 5

HCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 217079441-Cyclobutylmethanamine hydrochloride

생성물 1

HCID 576711932-(Cyclobutylmethyl-amino)-cyclopentanecarboxylic acid ethyl ester수율 79.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

2-Oxo-cyclopentanecarboxylic acid ethyl ester (0.24 mL, 1.64 mmol) and C-cyclobutyl-methylamine hydrochloride (0.20 g, 1.64 mmol) were dissolved in methanol (8 mL). Sodium acetate (0.27 g, 3.28 mmol) was added followed by 4 Å powdered molecular sieves (0.20 g) and sodium cyanoborohydride (0.21 g, 3.28 mmol). The reaction was stirred at 25° C. for 16 h. The mixture was poured into a mixture of saturated aqueous sodium bicarbonate solution (20 mL) and ethyl acetate (30 mL). After shaking, both layers were passed through a plug of Celite. The organic layer was further washed with saturated aqueous sodium bicarbonate solution (10 mL), saturated aqueous brine solution (10 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product, 2-(cyclobutylmethyl-amino)-cyclopentanecarboxylic acid ethyl ester (0.29 g, 1.30 mmol, 79%) as a clear oil. LC-MS (ESI) calcd for C13H23NO2 225.33, found 226.2 [M+H+].

후처리

  1. stirringAfter shaking
  2. washThe organic layer was further washed with saturated aqueous sodium bicarbonate solution (10 mL), saturated aqueous brine solution (10 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-39d5dcb038e94f0c92c9043f90f7fa5c
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582626B2

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