Tetrahydrofuran → (R)-[1-(4-Fluorophenyl)pyrrolidin-2-yl]methanamine

HRID 1477647Notes

Reaction equation

HRID 1477647 reaction equation
O1CCCC1.[NH2:6][CH2:7][C@@H:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:11](=O)[CH2:10][CH2:9]1.B.O1CCCC1>CO>[F:19][C:16]1[CH:17]=[CH:18][C:13]([N:12]2[CH2:11][CH2:10][CH2:9][C@@H:8]2[CH2:7][NH2:6])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuranHCID 96683900(R)-5-(Aminomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one

Product 1

HCID 117839679(R)-[1-(4-Fluorophenyl)pyrrolidin-2-yl]methanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a tetrahydrofuran solution (1.0 mL) of (R)-5-(aminomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one (50.0 mg, 0.240 mmol) synthesized in Reference Synthesis Example 216, borane-tetrahydrofuran complex (8.5% tetrahydrofuran solution) (0.760 mL, 0.720 mmol) was added and the resultant mixture was stirred at room temperature for 1 hour 30 minutes. Thereafter, the borane-tetrahydrofuran complex (1.0 mL) was further added and the resultant mixture was stirred at 70° C. for 1 day. After completion of the reaction, methanol was added to the reaction solution and the resultant mixture was stirred at 70° C. for 3 hours, followed by concentrating the reaction solution under reduced pressure to obtain a crude product of the title compound.

Workup

  1. additionwas added
  2. additionThereafter, the borane-tetrahydrofuran complex (1.0 mL) was further added
  3. additionwas added to the reaction solution
  4. concentrationby concentrating the reaction solution under reduced pressure

Sources & evidence

ORD record
ord-f8ab5cb833bc41aaaf6718d84f20fa02
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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