Potassium Cyanide → HCID 78035676, compound

HRID 1422603Notes

Reaction equation

HRID 1422603 reaction equation
CS(O[CH2:6][CH:7]1[CH2:9][C:8]1([NH:19][C:20]([O:22][CH3:23])=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)(=O)=O.[C-:24]#[N:25].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[C:24]([CH2:6][CH:7]1[CH2:9][C:8]1([NH:19][C:20](=[O:21])[O:22][CH3:23])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)#[N:25]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 86675583HCID 86675583, compound

Product 1

HCID 78035676HCID 78035676, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of ((1RS,2SR)-2-(methoxycarbonylamino)-2-(3-nitrophenyl)cyclopropyl)methyl methanesulfonate (intermediate B8a) (4.53 g, 13.2 mmol, Eq: 1.00), potassium cyanide (1.11 g, 17.1 mmol, Eq: 1.3) and tetrabutylammonium iodide (486 mg, 1.32 mmol, Eq: 0.1) in DMSO (13 ml) was stirred at 23° C. for 18 h. Poured into ice water, extracted with EtOAc, washed organic layer with brine, reextracted combined aqueous layer with EtOAc, dried combined organic layer over Na2SO4. Removal of the solvent in vacuum left a dark brown oil (8370-1/1; HPLC 1.775 min 60%, 2.070 min 27%, 2.262 min 13%). The crude material was purified by flash chromatography (silica gel, 50 g, 0% to 60% EtOAc in heptane) to give the methyl (1SR,2SR)-2-(cyanomethyl)-1-(3-nitrophenyl)cyclopropylcarbamate (2.318 g, 8.42 mmol, 64.0% yield) as a yellow gum. MS (ISP): m/z=276.1 [(M+H)+].

Workup

  1. extractionextracted with EtOAc
  2. washwashed organic layer with brine
  3. customdried
  4. customRemoval of the solvent in vacuum
  5. waitleft a dark brown oil (8370-1/1; HPLC 1.775 min 60%, 2.070 min 27%, 2.262 min 13%)
  6. customThe crude material was purified by flash chromatography (silica gel, 50 g, 0% to 60% EtOAc in heptane)

Sources & evidence

ORD record
ord-d7fd8c46a3c145d4b77eda53b47c7695
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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