Nitrogen → HCID 69671666, compound

HRID 714207Notes

Reaction equation

HRID 714207 reaction equation
N#N.Cl.[F:4][C@H:5]1[CH2:9][CH2:8][NH:7][CH2:6]1.Cl[CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16])[CH2:6]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 16217739(s)-3-Fluoropyrrolidine hydrochloride

Product 1

HCID 69671666HCID 69671666, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of (5)-3-fluoropyrrolidine hydrochloride (250 mg, 1.99 mmol) and 2-(2-chloroethoxy)ethanol (0.21 mL, 1.99 mmol) in dry toluene (7 mL) was added K2CO3 (1.51 g, 10.95 mmol) at rt followed by KI (33 mg, 0.20 mmol). The reaction mixture was stirred at reflux for 15 h. The mixture was filtered and the filtrate concentrated under reduced pressure to give crude (S)-2-(2-(3-fluoropyrrolidin-1-yl)ethoxy)ethanol as a yellow oil. TLC:rf (90:10:0.5 CH2Cl2-MeOH—NH4OH)=0.23.

Workup

  1. temperatureat reflux for 15 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-a8ffe5fcb9ec4242a7fe80c11c780d61
Source dataset
uspto-grants-2015_11
Patent number
US09187435B2

Reaction notes

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