4-(tert-Butoxycarbonylamino)piperidine

off-white crystalline powder

J-Butyl-l-benzylpiperidin-4-ylcarbamate (3.80 g, 13.1 mmol) obtained in Preparation Example 1-i was dissolved in 26 ml of methanol in a 100 ml vessel, and a catalytic quantity of 10percent active palladium/carbon was added thereto, and the resulting mixture was reacted under a hydrogen atmosphere for 12 hrs. After the completion of reaction, the reaction mixture was filtered through a cellite pad to remove the active palladium/carbon and the solvent was removed under reduced pressure therefrom. Then, the residue was subjected to a silica gel column chromatography to obtain 2.64 g of the title compound (yield 99percent).f-Butyl-l-benzylpiperidin-4-ylcarbamate (3.80 g, 13.1 mmol) obtained in Preparation Example I was dissolved in 26 ml of methanol in the 100 ml reaction vessel, catalytic quantities of 10percent active palladium/carbon was added thereto, and reacted under the hydrogen for 12 hrs. After the completion of the reaction, the reduction mixture was filtered through a cellite pad to remove palladium/carbon and the solvent was removed under a reduced pressure. Then, the mixture was subjected to silica gel column chromatography to obtain 2.64 g of the title compound (yield: 99percent).To a solution of the compound obtained in the above step (1) (72.6 g) in methanol (350 mL) was added 20 percent palladium-carbon (17.5 g) and the mixture was stirred at room temperature under hydrogen-gas atmosphere overnight. The reaction mixture was filtered by a membrane filter and the filtrate was concentrated in vacuo to obtain 4-(tert-butoxycarbonyl)aminopiperidine (48.3 g, yield: 96 percent) as a pale yellow solid. MS(APCI)m/z; 201 [M+H]Tert-butyl 1-benzylpiperidin-4-ylcarbamate (500 mg, 1.72 mmol) was dissolved in methanol (10 ml) and stirred. 36percent aqueous HCl (169 µl, 1.72 mmol) was added followed by Pd(OH)A solution of the ester 2 from above (66 g, 227.27 mmol) in 1 1 of ethanol is hydrogenated under normal pressure with 10 g of Pd/C (10percent) for 16 hours at room temperature. The mixture is filtered over celite and evaporated under reduced pressure. Recrystallisation from ether gave 34.5 g (76percent) of white crystals. MS (ESI) : 201 [M+H] +, 401 [2M+H] +, 1H-NMR (DMSO-d6) : b (ppm) 6.7 (br d, NH), 3.22 (br m, 1H), 2.88 (dt, 2H), 2.39 (dt, 2H), 1.8 (brs, NH), 1.6 (dt, 2H), 1.35 (s, 9H), 1.18 (dt, 2H).

Used as pharmaceutical intermediate

Molecular Weight:200.28
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:200.152477885
Monoisotopic Mass:200.152477885
Topological Polar Surface Area:50.4
Heavy Atom Count:14
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes