Methanol → HCID 53952369, compound

HRID 430824Notes

Reaction equation

HRID 430824 reaction equation
[C:1]([C:3]1[CH2:9][CH:8]2[N:10]([CH2:11][CH:12]([F:14])[F:13])[CH:5]([CH2:6][CH2:7]2)[CH:4]=1)#[N:2].CO.[BH4-].[Na+].P([O-])(O)(O)=O.[K+]>N1C=CC=CC=1>[C:1]([CH:3]1[CH2:4][CH:5]2[N:10]([CH2:11][CH:12]([F:14])[F:13])[CH:8]([CH2:7][CH2:6]2)[CH2:9]1)#[N:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 516951Monobasic potassium phosphateHCID 4311764Sodium borohydrideHCID 18352161HCID 18352161, compound

Product 1

HCID 53952369HCID 53952369, compoundYield 185,637.094%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An oven-dried 10 ml round bottom flask was fitted with a reflux condenser and a magnetic stirrer and placed under an atmosphere of nitrogen. 3-Cyano-8-(2,2-difluoroethyl)-8-azabicyclo[3.2.1]oct-2-ene (0.17 g, 0.53 mmol) was charged to the reactor followed by methanol (0.25 ml) and pyridine (0.75 ml) to give a solution. Solid sodium borohydride (0.039 g, 1.03 mmol) was added in a single portion and the mixture was then heated and held at reflux for 3 hour. After cooling to ambient, the reaction mass was poured into an agitated saturated aqueous potassium dihydrogen phosphate (10 ml) solution. The aqueous solution was extracted with dichloromethane (3×10 ml) and the combined organic layers were dried (Na2SO4). Concentration in vacuo to give 3-cyano-8-(2,2-difluoroethyl)-8-azabicyclo-[3.2.1]octane(0. 197 g, 95% yield) as a mixture of epimers (90:10 exo:endo).

Workup

  1. customAn oven-dried 10 ml round bottom flask was fitted with a reflux condenser and a magnetic stirrer
  2. customto give a solution
  3. temperaturethe mixture was then heated
  4. temperatureat reflux for 3 hour
  5. temperatureAfter cooling to ambient, the reaction mass
  6. extractionThe aqueous solution was extracted with dichloromethane (3×10 ml)
  7. dry with materialthe combined organic layers were dried (Na2SO4)
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-87ecea32925f4f188bafcc405364cf22
Source dataset
uspto-grants-2001_11
Patent number
US06323343B1

Reaction notes

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