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Triethylamine → trans(+/-)-Benzyl 3-(bis(tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate

HRID 1920159
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HRID 1920159 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:14]([OH:15])[CH2:13][CH2:12][N:11]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:26](C(OC(C)(C)C)=O)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=O.C(N(CC)CC)C>C(Cl)Cl.CC#N.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:26])[C@H:9]1[C@H:14]([OH:15])[CH2:13][CH2:12][N:11]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 53487823Benzyl (3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylate

생성물 1

HCID 131729680trans(+/-)-Benzyl 3-(bis(tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6342
Acetonitrile
용매
HCID 6344Dichloromethane용매

실험 절차

To a solution of trans(+/−)-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylate (1.0 equiv.) in DCM and CH3CN (1:1, 0.14 M) was added BOC2O (1.0 equiv.), triethylamine (1.5 equiv.), and DMAP (catalytic amount). The reaction was stirred at room temperature for 15 h, upon which time the solution was concentrated and purified via silica gel column chromatography eluting with EtOAc and hexanes (1:6) to give the desired product as a white foam. LCMS (m/z): 451.1 (MH+).

후처리

  1. concentrationwas concentrated
  2. custompurified via silica gel column chromatography
  3. washeluting with EtOAc and hexanes (1:6)

출처 및 근거

ORD 기록
ord-dbbe499fb90744e2bd3d857a86489ee8
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08168794B2

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