Trimethyl phosphonoacetate → 4-Cyclohexyl-4-(2-methoxycarbonyl-vinyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1795168노트

반응식

HRID 1795168 반응식
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[Cl-].[Li+].N12CN=CC1CCCC2.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][C:33]([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)([CH:36]=O)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(#N)C>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][C:33]([CH:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)([CH:36]=[CH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:32][CH2:31]1)=[O:29])([CH3:24])([CH3:25])[CH3:26]

참가 물질

6

반응물 4

HCID 80029Trimethyl phosphonoacetateHCID 433294Lithium ChlorideHCID 157889911,8-Diazabicyclo[4.3.0]non-7-eneHCID 219368754-Cyclohexyl-4-formylpiperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 695971104-Cyclohexyl-4-(2-methoxycarbonyl-vinyl)-piperidine-1-carboxylic acid tert-butyl ester수율 86%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of trimethyl phosphonoacetate (1.41 ml, 8.72 mmole), lithium chloride (477 mg, 11.3 mmole), and 1,8-diazabicyclo[4.3.0]non-7-ene (DBU) (1.55 ml, 11.3 mmole) in anhydrous acetonitrile (25 ml) is added 4-cyclohexyl-4-formyl-piperidine-1-carboxylic acid tert-butyl ester, 7, (2.58 mg, 8.72 mmole) under argon at room temperature. The mixture is stirred for one hour and the solvent then removed under reduced pressure. The crude product is purified over silica (methylene chloride:methanol=15:1, Rf=0.78) to afford 2.64 g (86% yield) of the desired compound.

후처리

  1. customthe solvent then removed under reduced pressure
  2. customThe crude product is purified over silica (methylene chloride:methanol=15:1, Rf=0.78)

출처 및 근거

ORD 기록
ord-94b6c078e4e946cab61a484cb6848c8b
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026335B2

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