Cyanomethylenetributylphosphorane → HCID 117690357, compound

HRID 1502090Notes

Reaction equation

HRID 1502090 reaction equation
O[CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:20]=1[CH3:28])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C@H:5]1[CH2:17][OH:18].C(C=P(CCCC)(CCCC)CCCC)#N>C1C=CC=CC=1>[CH3:28][C:20]1[C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=1[CH:2]1[O:18][CH2:17][C@@H:5]2[CH2:6][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:8][CH2:9][N:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 117690307HCID 117690307, compound

Product 1

HCID 117690357HCID 117690357, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

(3S)-tert-Butyl 4-(2-hydroxy-2-(2-methyl-3-nitrophenyl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate (2.15 g, 5.44 mmol) was dissolved in benzene (30 mL) then added cyanomethylenetribuylphosphorane (2.362 g, 9.79 mmol). The mixture was degassed then heated to 100° C. overnight. After cooling, the benzene was evaporated off and the residue was purified by chromatography through a 330 g ISCO Redi-sep column eluting with 5-10% acetone: methylene chloride to yield the title compound: LC-MS (IE, m/z): 378 [M+1]+

Workup

  1. customThe mixture was degassed
  2. temperatureAfter cooling
  3. customthe benzene was evaporated off
  4. customthe residue was purified by chromatography through a 330 g ISCO Redi-sep column
  5. washeluting with 5-10% acetone

Sources & evidence

ORD record
ord-c7251afcf54b440cabe0b70b9bd373eb
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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