Water → HCID 9804299, compound

HRID 842218Notes

Reaction equation

HRID 842218 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.[OH2:34]>C(Cl)(Cl)(Cl)Cl.CC#N>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([C:18]([OH:34])=[O:19])[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

5

Reactant 2

HCID 962Water2×HCID 18723500HCID 18723500, compound

Product 1

HCID 9804299HCID 9804299, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.126 g (0.28 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-hydroxymethyl pyrrolidine, 0.18 g (0.85 mmol) of NaIO4, and 0.0029 g (0.014 mmol) of RuCl3.3 H2O in 2 mL of CCl4, 3 mL of H2O and 2 mL of CH3CN was stirred at rt for 1 h. The reaction mixture was partitioned between CH2Cl2 and H2O. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated to give the title compound. 1H NMR (key peaks) (CDCl3) δ7.81-7.88 (m, 3H), 7.43-7.74 (m, 4H), 7.11-7.14 tm, 2H), 6.97 (t, 2H, J=8.0 Hz), Mass Spectrum (ESI) m/e=461 (M+1).

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 and H2O
  2. dry with materialThe organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3c9955a251dd4902b63217fc50b9a758
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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