Sodium Bicarbonate → C-Phenyl-C-(3-pyrrolidin-1-yl-oxetan-3-yl)-methylamine

HRID 560189Notes

Reaction equation

HRID 560189 reaction equation
[N:1]1([C:6]2([C:10]#[N:11])[CH2:9][O:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:12]1([Li])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>O1CCCC1>[C:12]1([CH:10]([NH2:11])[C:6]2([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH2:9][O:8][CH2:7]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 591979193-Cyano-3-(pyrrolidin-1-YL)oxetane2×HCID 178506676HCID 178506676, compound

Product 1

HCID 59197932C-Phenyl-C-(3-pyrrolidin-1-yl-oxetan-3-yl)-methylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Pyrrolidin-1-yl-oxetane-3-carbonitrile (intermediate A, 1.6 g, 91% purity, 10 mmol) was dissolved in 10 mL tetrahydrofurane. Phenyllithium (2M in dibutylether, 9.8 mL, 20 mmol) was added dropwise at −5° C. The reaction mixture was stirred at room temperature for 1.5 hours and poured into cold saturated sodium bicarbonate solution. The mixture was extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The residue was dissolved in 35 mL methanol and sodiumborohydride (0.77 g, 20 mmol) was added portion-wise at 0° C. The reaction mixture was stirred at room temperature for 2 hours and quenched by addition of water. The solvent was evaporated off. The residue was taken up in water and ethyl acetate and was extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude product (brown oil, 2.26 g, 99%) was used for the next step without further purification, MS: m/e=216.3 [(M−NH2)+].

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate
  2. customThe combined organic phases were dried on sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue was dissolved in 35 mL methanol
  6. stirringThe reaction mixture was stirred at room temperature for 2 hours
  7. customquenched by addition of water
  8. customThe solvent was evaporated off
  9. extractionethyl acetate and was extracted three times with ethyl acetate
  10. customThe combined organic phases were dried on sodium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. customThe crude product (brown oil, 2.26 g, 99%) was used for the next step without further purification, MS

Sources & evidence

ORD record
ord-e2152e1c1c12418e91a40e92a7bbc5bd
Source dataset
uspto-grants-2011_11
Patent number
US08063098B2

Reaction notes

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