Cyanomethylenetributylphosphorane → HCID 86727072, compound

HRID 2175850Notes

Reaction equation

HRID 2175850 reaction equation
[C:1]([C:3]1[C:4]([O:28][CH3:29])=[C:5]([CH:10]([OH:27])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@H:13]2[CH2:25]O)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C(C=P(CCCC)(CCCC)CCCC)#N>C1C=CC=CC=1>[C:1]([C:3]1[C:4]([O:28][CH3:29])=[C:5]([CH:10]2[O:27][CH2:25][C@@H:13]3[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:16][CH2:17][N:12]3[CH2:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

4

Reactant 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 86727071HCID 86727071, compound

Product 1

HCID 86727072HCID 86727072, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl (3S)-4-[2-(3-cyano-4-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate (2 g, 4.88 mmol) and cyanomethylenetri-n-butylphosphorane (2.122 g, 8.79 mmol) were dissolved in 15 mL benzene. The reaction mixture was degassed and heated to 100° C. for 16 hrs. LC-MS showed product peak at 2.07 (M+1=380). The reaction was cooled and evaporated to dryness. The residue was chromatographed through a 80 g Redi-sep column and eluted with 40% EtOAc/60% hexane mixture to yield cis-trans mixture of the title compound.

Workup

  1. customThe reaction mixture was degassed
  2. temperatureThe reaction was cooled
  3. customevaporated to dryness
  4. customThe residue was chromatographed through a 80 g Redi-sep column
  5. washeluted with 40% EtOAc/60% hexane mixture
  6. customto yield

Sources & evidence

ORD record
ord-ea9ec32665744c449306789a6fc2726d
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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