(R)-3-(Boc-Amino)piperidine

White powder

46.8 g of compound IV, 2.3 g of 10percent wet palladium on carbon (water content 50percent) and 320 mL of methanol were added to the autoclave.Nitrogen replacement for 3 to 4 times, charging with hydrogen at a pressure of 0.3 to 0.4 MPa, raising the temperature to 35 to 40 ° C, and keeping the reaction for 2 h.The HPLC was traced to completion of the conversion of the starting material, filtered, concentrated to a fraction free, and 23 mL of dichloromethane and 46 mL of petroleum ether were added.Warm up to 35 ~ 40 ° C, slowly add 325 mL of petroleum ether at this temperature, keep warm for 1 h, Slowly cool down to -5 to 0 ° C, filter, and dry at 40 to 45 ° C to obtain 26.7 g of white (R)-3-Boc-aminopiperidine.The yield was 95.4percent.(R) [PIPERIDIN-3-VL-CARBAMIC] acid [TERT.-BUTYL] ester (R) [3-TERT-BUTOXYCARBONYLAMINO-PIPERIDINE-1-CARBOXYLIC] acid benzyl ester (50 g, 150 [MMoL)] was dissolved in abs. [ETOH] (500 [ML), ] and hydrogenated (1 atm, 7 days, 10 percent Pd/C (5.0 g) ) at RT. The reaction was filtered and evaporated in vacuo to give the product as a white solid. Yield 27.3 g [(92 percent).] 'H-NMR (dmso-d6, 300 MHz) [6] [6.] 85 (d, [1 H), ] 3.41 (s br, 2H), 3.05 (m, [1 H), ] 2.90 (m, [1 H), ] 2. [58-2.] 35 (m, 2H), 1.92 (m, 1 H), 1.75 (m, 1 H), 1.58 (s, 9H), 1.50-1. 40 (m, 2H). For analysis a small sample of the product (50 mg) was dissolved in EtOAc (2 [ML), ] treated with 3 N HCI in EtOAc (2 [ML), ] and evaporated in vacuo. The product was stirred with EtOAc (5 ml) for one hour and filtered to give (R) 3-aminopiperidine in > 98 percent ee, (determined as described in method G).2(R) -3-tert-butoxycarbonylamino-1-benzylpiperidine prepared in Example 4 was added, and thereto was added 10 g of a palladium Carbon (palladium content of the mass fraction of 10percent, moisture content of 53percent), installed after the kettle cover, hydrogen replacement system three times, to maintain the system pressure of about 1.5 atmospheric pressure, temperature 45 ° C, reaction 2 hours, with nitrogen replacement system three times, The filtrate was filtered through an appropriate amount of diatomaceous earth and the filtrate was spin dried to give (R) -3-tert-butoxycarbonylaminopiperidine, weighing 146 g, 85percent yield.A mixture was obtained by mixing 96. 5 g (0.274 mol, optical purity 97.4percent ee (R form)) of the diastereomer salt of t-butyl (R)-piperidin-3-ylcarbamate and, R-mandelic acid obtained in Example 31-2 with 12.5 g of sodium chloride, 97 ml of water, and 193 ml of 1-butanol. While maintaining the obtained mixture at 10 to 30°C, 115 g (0.287 mol) of an aqueous solution of 10 wtpercent sodium hydroxide was added thereto, and the resultant was stirred. An organic layer was obtained by a liquid-separation process. The water layer was extracted with 97 ml of 1-butanol, and the obtained organic layer and the organic layer previously obtained were mixed. The obtained organic layer was washed twice with 97 mL of water, and the obtained organic layer was concentrated under reduced pressure. To the concentration residue, 297 mL of 4-methyl-2-pentanone was added, and the obtained mixture was partially concentrated, whereby crystals were deposited. The crystals were collected by filtration and washed with 107 ml of ethyl acetate. By drying the obtained crystals, 43.7 g of t-butyl (R)-piperidin-3-ylcarbamate was obtained as a white crystal, with a yield of 79.7percent. The obtained t-butyl piperidin-3-ylcarbamate was derivatized with use of 3, 5-dinitrobenzoyl chloride and analyzed by high-speed liquid chromatography, whereby the optical purity of the t-butyl piperidin-3-ylcarbamate was 99.8percent ee (R form).

(R)-3-Boc-aminopiperidine is a chemical substance, an intermediate in organic synthesis and a pharmaceutical intermediate, which can be used in the laboratory organic synthesis process and the development of chemical medicine, as a production of aglitin, Ringer An intermediate of leutin to synthesize alogliptin benzoate.

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:199
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes