Dichloromethane → (S)-2-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yloxy)ethanamine

HRID 874073Notes

Reaction equation

HRID 874073 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([O:13][CH2:14][CH2:15][NH:16]C(=O)OC(C)(C)C)[CH:10]=[N:11][CH:12]=1.C(Cl)Cl>FC(F)(F)C(O)=O>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([O:13][CH2:14][CH2:15][NH2:16])[CH:10]=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 58537431(S)-tert-butyl 2-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yloxy)ethylcarbamate

Product 1

HCID 54675478(S)-2-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yloxy)ethanamineYield 85%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Preparation 12a: (S)-tert-butyl 2-(5-(1-Methylpyrrolidin-2-yl)pyridin-3-yloxy)ethylcarbamate (preparation 11) (105 mg, 0.33 mmol) was stirred in trifluoroacetic acid (1 mL) and DCM (5 mL) for 1.5 h. The reaction mixture was evaporated, then co-evaporated with DCM (×5) and 20% ammonia in MeOH. The crude product was purified by flash chromatography (5% [20% ammonia in MeOH] in DCM) to give the title compound as a yellow oil (62 mg, 85%).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe crude product was purified by flash chromatography (5% [20% ammonia in MeOH] in DCM)

Sources & evidence

ORD record
ord-4a9d04f5ab4c4feea4fd7650066e6039
Source dataset
uspto-grants-2015_03
Patent number
US08980276B2

Reaction notes

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