1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(2-Cyanovinyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester

HRID 1795174Notes

Reaction equation

HRID 1795174 reaction equation
C[C:2](C)(P(O)(O)=O)[C:3]#[N:4].[Li+].[Cl-].C1CCN2C(=NCCC2)CC1.[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:36]=[CH:2][C:3]#[N:4])([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 20250566Dimethyl phosphono acetonitrileHCID 219368754-Cyclohexyl-4-formylpiperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 695970864-(2-Cyanovinyl)-4-cyclohexylpiperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of dimethyl phosphono acetonitrile (0.78 mL, 4.02 mmol), LiCl (184 mg, 4.02 mmol), and DBU (0.55 mL, 4.02 mmol) in anhydrous acetonitrile (25 mL) is added 4-cyclohexyl-4-formylpiperidine-1-carboxylic acid tert-butyl ester, 7, (992 mg, 3.35 mmol) under an atmosphere of argon at room temperature. The mixture is stirred for 1 hour and the solvent removed in vacuo. The resulting crude product is purified over silica gel eluting with dichloromethane/methanol 15:1 to afford the desired product in quantitative yield.

Workup

  1. customthe solvent removed in vacuo
  2. customThe resulting crude product is purified over silica gel eluting with dichloromethane/methanol 15:1

Sources & evidence

ORD record
ord-1a82d21f30c24478afcca70c9e47fd61
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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