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With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20.0℃;
To a stirred solution of (3S,4R)piperidine XVII and cyclohexanone in DCE were added NaBH(OAc)3 and AcOH and the reaction mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate and washed with brine (2X). The organic phase was concentrated, and the product purified by CC using CH2Cl2/MeOH (9:1) to furnish amine XVIII in 75% yield.
tert-butyl (3S,4R)-4-[(benzyloxy)carbonyl]amino}-3-methoxypi peridine-1-carboxylate[ No CAS ]
[ 1171125-92-0 ]
Yield
Reaction Conditions
Operation in experiment
97%
With palladium 10% on activated carbon; In methanol; at 20.0℃; for 1.3h;Inert atmosphere;
10% palladium-carbon (108 g) was added to a solution of the secondeluting peak compound obtained in Step 2 (230 mg, 0.631 mmol) in methanol(7 mL), and the mixture was stirred under a hydrogen gas atmosphere at room temperature for 1 hour and 30 minutes. The reaction solution, from which the catalyst was removed by filtration, was concentrated under reduced pressure to obtain title compound (141 mg, 97%) as a colorless oily substance.
97%
With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃; for 1.5h;
10% Palladium-carbon (108 g) was added to a solution of the second-eluting peak compound obtained in Step 2 (230 mg, 0.631 mmol) in methanol (7 mL), and the mixture was stirred under a hydrogen gas atmosphere at room temperature for 1 hour and 30 minutes. The reaction solution, from which the catalyst was removed by filtration, was concentrated under reduced pressure to obtain title compound (141 mg, 97%) as a colorless oily substance.
di-tert-butyl [4-chloro-5-ethyl-2-({(3S,4R)-1-[5-(2-hydroxypropan-2-yl)-1,3,4-thiadiazol-2-yl]-3-methoxypiperidin-4-yl}carbamoyl)-1H-imidazol-1-yl]methyl phosphate[ No CAS ]
di-tert-butyl [5-chloro-4-ethyl-2-({(3S,4R)-1-[5-(2-hydroxypropan-2-yl)-1,3,4-thiadiazol-2-yl]-3-methoxypiperidin-4-yl}carbamoyl)-1H-imidazol-1-yl]methyl phosphate[ No CAS ]
(4-chloro-2-[(3S,4R)-1-{5-[(2R)-1,2-dihydroxypropan-2-yl]-1,3,4-thiadiazol-2-yl}-3-methoxypiperidin-4-yl]carbamoyl}-5-ethyl- 1H-imidazol-1-yl)methyl dihydrogen phosphate[ No CAS ]
[4-chloro-5-ethyl-2-({(3S,4R)-1-[5-(2-hydroxypropan-2-yl)-1,3,4-thiadiazol-2-yl]-3-methoxypiperidin-4-yl}carbamoyl)-1H-imidazol-1-yl]methyl dihydrogen phosphate[ No CAS ]
[5-chloro-4-ethyl-2-({(3S,4R)-1-[5-(2-hydroxypropan-2-yl)-1,3,4-thiadiazol-2-yl]-3-methoxypiperidin-4-yl}carbamoyl)-1H-imidazol-1-yl]methyl dihydrogen phosphate[ No CAS ]
di-tert-butyl (4-chloro-2-[(3S,4R)-1-{5-[(2R)-1,2-dihydroxypropan-2-yl]-1,3,4-thiadiazol-2-yl}-3-methoxypiperidin-4-yl]carbamoyl}-5-ethyl-1H-imidazol-1-yl)methyl phosphate[ No CAS ]
di-tert-butyl (5-chloro-2-[(3S,4R)-1-{5-[(2R)-1,2-dihydroxypropan-2-yl]-1,3,4-thiadiazol-2-yl}-3-methoxypiperidin-4-yl]carbamoyl}-4-ethyl-1H-imidazol-1-yl)methyl phosphate[ No CAS ]
di-tert-butyl (4-chloro-5-ethyl-2-[(3S,4R)-1-{5-[(1S)-1-hydroxyethyl]-1,3,4-thiadiazol-2-yl}-3-methoxypiperidin-4-yl]carbamoyl}-1H-imidazol-1-yl)methyl phosphate[ No CAS ]
di-tert-butyl (5-chloro-4-ethyl-2-[(3S,4R)-1-{5-[(1S)-1-hydroxyethyl]-1,3,4-thiadiazol-2-yl}-3-methoxypiperidin-4-yl]carbamoyl}-1H-imidazol-1-yl)methyl phosphate[ No CAS ]
monosodium [4-chloro-5-ethyl-2-({(3S,4R)-1-[5-(2-hydroxypropan-2-yl)-1,3,4-thiadiazol-2-yl]-3-methoxypiperidin-4-yl}carbamoyl)-1H-imidazol-1-yl]methyl dihydrogen phosphate[ No CAS ]
[4-chloro-5-ethyl-2-({(3S,4R)-1-[5-(2-hydroxypropan-2-yl)-1,3,4-thiadiazol-2-yl]-3-methoxypiperidin-4-yl}carbamoyl)-1H-imidazol-1-yl]methyl dihydrogen phosphate diethanolamine salt[ No CAS ]
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl acetamide; at 70.0℃; for 1.0h;
tert-Butyl (3S,4R)-4-amino-3-methoxypiperidine- l-carboxylate (224.4 mg, 0.96 mmol) obtained in Step 3 above, 4-chloro-5-ethyl-lH- imidazole-2-carboxylate (140 mg, 0.80 mmol) synthesized by the method described in the literature (WO 2009/084614), EDCI (440 mg, 2.29 mmol) and HOBT (110 mg, 0.81 mmol) were mixed in dimethylacetamide, and the mixture was heated at 70 C for 1 hour. The reaction solution was diluted with ethyl acetate, washed with water 3 times and with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column (ethyl acetate-hexane) to obtain title compound (222.4 mg, 72%) as a white solid.
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