Boron trifluoride etherate → Benzyl 4-chloro-3-(diethoxyphosphorylamino)piperidine-1-carboxylate

HRID 73563노트

반응식

HRID 73563 반응식
[CH2:1]([O:3][P:4]([N:9]1[CH:15]2[CH:10]1[CH2:11][CH2:12][N:13]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:14]2)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[ClH:26].C(N(CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[Cl:26][CH:10]1[CH2:11][CH2:12][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:14][CH:15]1[NH:9][P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:1][CH3:2])=[O:5]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 11130Triethylamine hydrochlorideHCID 59455678Benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate

생성물 1

HCID 67500461Benzyl 4-chloro-3-(diethoxyphosphorylamino)piperidine-1-carboxylate수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate (1.0 equiv.) and triethyl amine hydrochloride (4 equiv.) in DCM (0.1M) was added BF3.OEt2 (2.0 equiv.) and the reaction was allowed to stir at room temperature for 2 h under a nitrogen atmosphere. The solution was then quenched with water and extracted with DCM. The crude product was purified via silica gel column chromatography (ISCO eluting with EtOAc and Hexanes 50% to 100% EtOAc) to yield benzyl 4-chloro-3-(diethoxyphosphorylamino)piperidine-1-carboxylate in 89% yield. LCMS (m/z): 405.1 (MH+), Rt=2.73 min.

후처리

  1. customThe solution was then quenched with water
  2. extractionextracted with DCM
  3. customThe crude product was purified via silica gel column chromatography (ISCO eluting with EtOAc and Hexanes 50% to 100% EtOAc)

출처 및 근거

ORD 기록
ord-65a2bd7f7551455a8cb6f9c705a5269e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829193B2

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