Cyclopropylamine → Ethyl 4-(cyclopropylamino)cyclohexanecarboxylate

HRID 574916Notes

Reaction equation

HRID 574916 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH:13]1([NH2:16])[CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:13]1([NH:16][CH:2]2[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67126892Ethyl 4-(cyclopropylamino)cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 4-oxocyclohexanecarboxylate (3.4 g) in dichloromethane (30 mL) was added cyclopropanamine (1.14 g) followed by sodium triacetoxyborohydride (4.24 g). The mixture was stirred overnight. The mixture was diluted with dichloromethane (300 mL) and washed with 2N NaOH, water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the title compound.

Workup

  1. washwashed with 2N NaOH, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-e8d1e7dfd7604f53996aad5c72c43e7e
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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