Sodium cyanoborohydride → 2-(2-Dimethylamino-ethylideneamino)-cyclopentanecarboxylic acid ethyl ester
Reaction equation
[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]Participants
7
Reactant 2
Product 2
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
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+].
Workup
- washwashed twice with saturated aqueous sodium bicarbonate solution (100 mL)
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c5a69d51909f49859b405fe289700a0b
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582626B2
Reaction notes
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