对氟苯甲醛 → cis-2-(4-Fluoro-benzylamino)-cycloheptanecarboxylic acid methyl ester

HRID 731237笔记

反应方程式

HRID 731237 反应方程式
Cl.[CH3:2][O:3][C:4]([C@@H:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[NH2:13])=[O:5].C([O-])(=O)C.[Na+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[CH3:2][O:3][C:4]([C@@H:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[NH:13][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([F:19])=[CH:21][CH:22]=1)=[O:5]

参与物

8

反应物 5

HCID 68023对氟苯甲醛HCID 516892碳酸氢钠HCID 517045醋酸钠HCID 5003444氰基硼氢化钠HCID 66658076rac-methyl (1R,2S)-2-aminocycloheptane-1-carboxylate hydrochloride

产物 1

HCID 69062626cis-2-(4-Fluoro-benzylamino)-cycloheptanecarboxylic acid methyl ester收率 52%

试剂、催化剂与溶剂 2

HCID 887Methanol溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
25 °C

实验过程

cis-2-Amino-cycloheptanecarboxylic acid methyl ester hydrochloride (0.8 g, 3.86 mmol) was suspended in methanol (20 mL). Sodium acetate (0.63 g, 7.7 mmol) was added followed by 4 Å powdered molecular sieves (0.8 g) followed by 4-fluoro-benzaldehyde (0.48 g, 3.86 mmol). Sodium cyanoborohydride (0.48 g, 7.7 mmol) was added and the mixture stirred at 25° C. for 16 h. The mixture was poured into a 1:1 mixture of saturated aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL). After shaking, both layers were passed through a plug of Celite. The organic layer was further washed with saturated aqueous brine solution (50 mL), dried over magnesium sulfate and concentrated in vacuo to afford the crude product, cis-2-(4-fluoro-benzylamino)-cycloheptanecarboxylic acid methyl ester (0.56 g, 2 mmol, 52%), as a clear oil. LC-MS (ESI) calcd for C16H22FNO2 279.16, found 280.3 [M+H+].

后处理

  1. stirringAfter shaking
  2. washThe organic layer was further washed with saturated aqueous brine solution (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-a68860372c174cc8aafdf6fef6d3c5de
来源数据集
uspto-grants-2009_09
专利号
US07582626B2

反应笔记

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