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Cesium carbonate → Methyl cis(+/-)-3-(4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidin-1-yl)benzoate

HRID 1425256
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HRID 1425256 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18](OC(C)(C)C)=O)[CH2:14][C@H:13]1[O:25][CH2:26][CH2:27][CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)(=[O:32])C.C(O[C@H]1[C@@H](N[C:47](=O)[O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=C[CH:51]=2)CCNC1)CC.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+]>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:51]=[C:50]([CH:55]=[CH:54][CH:53]=2)[C:49]([O:48][CH3:47])=[O:32])[CH2:14][C@H:13]1[O:25][CH2:26][CH2:27][CH3:28])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 21866389Hydrogen chloride-ethyl acetateHCID 86648603tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidine-1-carboxylateHCID 86712357Benzyl cis(+/-)-[3-propoxypiperidin-4-yl]carbamate

생성물 1

HCID 86648737
Methyl cis(+/-)-3-(4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidin-1-yl)benzoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매

실험 절차

tert-Butyl cis(±)-4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidine-1-carboxylate obtained in Example (113e) (200 mg, 0.51 mmol) was dissolved in methanol (9 mL). A 4 N hydrochloric acid/ethyl acetate solution (6 mL) was added, and the mixture was stirred at room temperature for one hour. Following concentration under reduced pressure, the same operation as in Example (42a) was performed using the resulting benzyl cis(±)-[3-propoxypiperidin-4-yl]carbamate, methyl 3-bromo-5-benzoate (132 mg, 0.61 mmol), palladium acetate (11.4 mg, 0.05 mmol), BINAP (63.5 mg, 0.1 mmol) and cesium carbonate (498 mg, 1.53 mmol), to obtain 78 mg of the title compound as a pale yellow oily substance (36%).

후처리

  1. concentrationconcentration under reduced pressure

출처 및 근거

ORD 기록
ord-2bd9294f1fdf48909997bae445cb2506
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927588B2

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