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

HRID 1795168Notes

Reaction equation

HRID 1795168 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-94b6c078e4e946cab61a484cb6848c8b
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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