Cyclohexanone → Ethyl1-[(cyclohexylamino)methyl]cyclopropane-1-carboxylate

HRID 2234522Notes

Reaction equation

HRID 2234522 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:9][NH2:10])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([CH2:9][NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 7967CyclohexanoneHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 11480505Ethyl 1-(aminomethyl)cyclopropanecarboxylate2×

Product 1

HCID 68682361Ethyl1-[(cyclohexylamino)methyl]cyclopropane-1-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl1-(aminomethyl)cyclopropane-1-carboxylate (Intermediate 114; 20.65 g, 50 mmol) in DCM (200 mL) was added cyclohexanone (Aldrich; 5.28 mL, 51 mmol). After stirring at room temperature for 15 minutes, sodium acetate (4.185 g, 75 mmol) was added, followed by sodium triacetoxyborohydride (15.905 g, 75 mmol). The suspension was stirred at room temperature for 2 days then partitioned between DCM and saturated aqueous sodium hydrogen carbonate solution. The organic solution was dried over sodium sulphate and evaporated to yield the title compound as a colourless oil (7.2 g, 64%).

Workup

  1. stirringThe suspension was stirred at room temperature for 2 days
  2. customthen partitioned between DCM and saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic solution was dried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-5feb92c5ffae41a8879749e7f576499e
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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