Sodium Cyanide → HCID 178483638, compound

HRID 967211Notes

Reaction equation

HRID 967211 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:23])[CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17]OS(C)(=O)=O)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:24]#[N:25].[Na+]>CN(C)C=O.CCOCC>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][C:24]#[N:25])[CH2:13][CH2:12]1)[CH3:23])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 178483660HCID 178483660, compound

Product 1

HCID 178483638HCID 178483638, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 12.64 g (36.17 mmol) of trans-methanesulfonic acid 4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexylmethyl ester (example 13.1) and 4.51 g (92 mmol) of sodium cyanide in 100 ml of dimethylformamide was stirred for 6 hours at 110° C. The reaction mixture was then taken up in ether and washed four times with water. The ether layer was dried over sodium sulfate and concentrated under reduced pressure, giving 10.14 g of crude trans-[2-(4-cyanomethyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester as a colorless oil, which was used without further purification.

Workup

  1. washwashed four times with water
  2. dry with materialThe ether layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef1029ffbe8c4c11bb79df74f49eba45
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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