Cesium carbonate → Methyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylpyridine-3-carboxylate

HRID 43771

반응식

HRID 43771 반응식
Cl.[CH3:2][O:3][C@H:4]1[C@@H:9]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7][NH:6][CH2:5]1.Cl[C:22]1[CH:23]=[C:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([CH3:28])=[N:26][CH:27]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:13]([O:12][C:11]([NH:10][C@H:9]1[CH2:8][CH2:7][N:6]([C:22]2[CH:23]=[C:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([CH3:28])=[N:26][CH:27]=2)[CH2:5][C@H:4]1[O:3][CH3:2])=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 10867045Methyl 5-chloro-2-methylnicotinateHCID 86648698Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate hydrochloride

생성물 1

HCID 86648719Methyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylpyridine-3-carboxylate수율 86.4%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

The same operation as in Example (42a) was performed using benzyl cis(±)-[3-methoxypiperidin-4-yl]carbamate hydrochloride obtained in Example (160a) (190 mg, 0.63 mmol), methyl 5-chloro-2-methylpyridine-3-carboxylate (117 mg, 0.63 mmol), palladium acetate (14.2 mg, 0.06 mmol), BINAP (78.6 mg, 0.13 mmol) and cesium carbonate (617 mg, 1.89 mmol), to obtain 225 mg of the title compound as a brown oily substance (86%).

출처 및 근거

ORD 기록
ord-dc8f50306dd3463c81a28cf1cc156f80
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536197B2

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