Diethyl Ether → HCID 18335086, compound

HRID 842222Notes

Reaction equation

HRID 842222 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH2:18][OH:19])[CH:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].CI.[CH3:38]COCC>CS(C)=O>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH2:18][O:19][CH3:38])[CH:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[CH2:23][CH2:22]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 18723500HCID 18723500, compound

Product 1

HCID 18335086HCID 18335086, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.025 g (0.057 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-hydroxymethylpyrrolidine, 0.013 g (0.23 mmol) of KOH and 0.028 mL (0.46 mmol) of methyl iodide in 2 mL of DMSO was stirred at rt for 1.2 h. The reaction mixture was poured into ether and washed with sat'd NaHCO3 and NaCl solutions, dried over Na2SO4 and filtered. The filtrate was concentrated and the residue was purified by chromatography (silica, acetone:hexanes, 1:2) to give the title compound. Mass Spectrum (ESI) m/e=461 (M+1).

Workup

  1. washwashed with sat'd NaHCO3 and NaCl solutions
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography (silica, acetone:hexanes, 1:2)

Sources & evidence

ORD record
ord-6586485c791444e6b7ad6b24b5570b17
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

Loading…