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

HRID 73563ノート

反応式

HRID 73563 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-65a2bd7f7551455a8cb6f9c705a5269e
出典データセット
uspto-grants-2014_09
特許番号
US08829193B2

反応ノート

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