(1-AMINOMETHYL-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER synthesis

Yield:864943-63-5 83%

Reaction Conditions:

Stage #1: 1-(tert-butoxycarbonylamino)cyclohexan-1-carboxamidewith dimethylsulfide borane complex in tetrahydrofuran;toluene; for 4 h;Heating / reflux;
Stage #2: with hydrogenchloride in tetrahydrofuran;water;toluene;
Stage #3: with sodium hydroxide in tetrahydrofuran;water;toluene; pH=> 12;

Steps:

2

Step 2 The solution of amide 5014b (8. 35 g, 34.5 mmol) in anhydrous THF (100 mL) at rt was added a solution of borane methyl sulfide complex in toluene (43.0 mL, 86.0 mmol) and the mixture was refluxed for 4 h. More THF (100 mL) was added and 3 N HCI solution was added slowly until no gas evolution was observed. To the mixture was added 50% w/w NaOH solution slowly until PH is greater than 12. Ether (200 mL) was then added and layers were separated. The aqueous solution was extracted with THF/diethyl ether (1: 1,150 mL) twice. Organic solutions were combined, dried (MgS04), filtered and concentrated to give 6.50 g of the product 5014c (83%).

References:

WO2005/85242,2005,A1 Location in patent:Page/Page column 91