Acetone → Ethyl1-[(propan-2-ylamino)methyl]cyclopropane-1-carboxylate

HRID 2234478Notes

Reaction equation

HRID 2234478 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:9][NH2:10])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:11][C:12]([CH3:14])=O.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:12]([CH3:14])[CH3:11])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 11480505Ethyl 1-(aminomethyl)cyclopropanecarboxylate2×

Product 1

HCID 68684554Ethyl1-[(propan-2-ylamino)methyl]cyclopropane-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl1-(aminomethyl)cyclopropane-1-carboxylate (Intermediate 114; 20.65 g, 250 mmol) in DCM (200 mL) was added acetone (3.74 mL, 51 mmol). After stirring at room temperature for 15 minutes, sodium acetate (4.185 g, 51 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 an aqueous solution of saturated sodium hydrogen carbonate. The organic layer was separated, then dried over sodium sulphate evaporated to yield the title compound as a clear oil (9.2 g, 100%).

Workup

  1. stirringThe suspension was stirred at room temperature for 2 days
  2. customthen partitioned between DCM
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-fb757664b412412395c7580d164fdcc6
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

Loading…