Methyl iodide → HCID 18388399, compound

HRID 842224Notes

Reaction equation

HRID 842224 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH:18]([OH:20])[CH3:19])[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]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+].[CH3:37]I>CS(C)=O.CCOCC>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH:18]([O:20][CH3:37])[CH3:19])[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[CH2:24][CH2:23]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 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 18723463HCID 18723463, compound

Product 1

HCID 18388399HCID 18388399, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.026 g (0.057 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(1-hydroxyethyl)pyrrolidine (diastereomer 2), 0.012 mg (0.23 mmol) of KOH and 0.0042 mL (0.068 mmol) of methyliodide in 1 mL of DMSO was stirred at rt for 30 min. The reaction mixture was diluted with ether and washed with sat'd NaHCO3 and NaCl solutions. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated and purified by chromatography (silica, hexanes:ethylacetate:(2N NH3 in MeOH), 10:10:1) to give the title compound. 1H NMR (CDCl3) δ (key peaks) 7.88-7.91(m, 3H), 7.45-7.55 (m, 4H), 7.20 and 7.10 (d of d, 2H, J=5.5, 8.5 Hz), 7.00 and 6.95 (t, 2H, J=9.0 Hz), 3.40 and 3.24 (s, 3H) 1.25 and 1.02 (d, 3H, J=6.5 Hz), Mass Spectrum (ESI) m/e=475 (M+1).

Workup

  1. washwashed with sat'd NaHCO3 and NaCl solutions
  2. dry with materialThe organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. custompurified by chromatography (silica, hexanes:ethylacetate:(2N NH3 in MeOH), 10:10:1)

Sources & evidence

ORD record
ord-857bc7279f1e4bfb9bf4e8dda69ed5d4
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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