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

HRID 731356ノート

反応式

HRID 731356 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-39d5dcb038e94f0c92c9043f90f7fa5c
出典データセット
uspto-grants-2009_09
特許番号
US07582626B2

反応ノート

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