Sodium Cyanide → HCID 178453919, compound

HRID 711972Notes

Reaction equation

HRID 711972 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]1)(=O)=O.[C-:21]#[N:22].[Na+]>CS(C)=O>[C:21]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9][CH2:8]1)#[N:22]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 178453973HCID 178453973, compound

Product 1

HCID 178453919HCID 178453919, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of {trans-4-[(tert-butoxycarbonyl)amino]cyclohexyl}methyl methanesulfonate (1.48 g, 4.81 mmol) and sodium cyanide (0.46 g, 9.4 mmol) in dimethyl sulfoxide (20 mL) was stirred at 90° C. for 4 h. After cooling, the mixture was partitioned between EtOAc and brine. The organic layer was washed with water, concentrated and purified on silica gel (eluting with 50% EtOAc in hexanes) to give tert-butyl [trans-4-(cyanomethyl)cyclohexyl]carbamate. LCMS calculated for C13H22N2O2Na (M+Na)+: m/z=261.2. Found: 261.1. A solution of the Boc-protected intermediate in methylene chloride (20 mL) was treated with trifluoroacetic acid (3 mL, 40 mmol) and the resulting mixture was stirred at room temperature for 2 h, then concentrated to give the desired product as TFA salt. LCMS calculated for C8H15N2 (M+H)+: m/z=139.1. Found: 139.1.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between EtOAc and brine
  3. washThe organic layer was washed with water
  4. concentrationconcentrated
  5. custompurified on silica gel (eluting with 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6a559a3a26634259bfad1dfdc7492f70
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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