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

HRID 1795168ノート

反応式

HRID 1795168 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-94b6c078e4e946cab61a484cb6848c8b
出典データセット
uspto-grants-2006_04
特許番号
US07026335B2

反応ノート

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