Sodium Cyanide → HCID 21023772, compound

HRID 1795171Notes

Reaction equation

HRID 1795171 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)([CH2:14][CH2:15][CH:16]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S([CH2:34][N+:35]#[C-:36])(C1C=CC(C)=CC=1)(=O)=O.[C-]#[N:38].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)([CH2:14][CH2:15][C:16]2[NH:38][CH:34]=[N:35][CH:36]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 161915Tosylmethyl isocyanideHCID 21023777HCID 21023777, compound

Product 1

HCID 21023772HCID 21023772, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-cyclohexyl-4-(3-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester, 10, (300 mg, 0.93) in ethanol (10 ml) is treated with tosylmethyl isocyanide (tosMIC) (176 mg, 0.93 mmole) and sodium cyanide (6 mg) at room temperature for three hours. The solvent is removed under reduced pressure and ammonia in methanol (2M, 10 ml) added. The mixture is stirred in a sealed tube overnight. The reaction mixture is then concentrated under reduced pressure and the residue taken up in chloroform, washed with aqueous sodium bicarbonate, brine, then dried with sodium sulfate and concentrated to a red oil. The residue is purified over silica (methylene chloride:methanol=15:1, Rf=0.58) to afford 141 mg (42% yield) of the desired product.

Workup

  1. customThe solvent is removed under reduced pressure and ammonia in methanol (2M, 10 ml)
  2. additionadded
  3. concentrationThe reaction mixture is then concentrated under reduced pressure
  4. washwashed with aqueous sodium bicarbonate, brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated to a red oil
  7. customThe residue is purified over silica (methylene chloride:methanol=15:1, Rf=0.58)

Sources & evidence

ORD record
ord-ccdd26bae6114da5aa40a2155169759f
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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