Dichloromethane → HCID 18723505, compound

HRID 842221Notes

Reaction equation

HRID 842221 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.F[C:7](F)(F)[C:8](O)=O.[C:13]1([C:23]([N:25]2[CH2:29][CH:28](CCO)[CH:27]([CH2:33][N:34]3[CH2:39][CH2:38][CH:37]([C:40]4[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=4)[CH2:36][CH2:35]3)[CH2:26]2)=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[CH2:47](Cl)Cl>CC([O-])=O.CC([O-])=O.[Cu+2]>[C:13]1([C:23]([N:25]2[CH2:29][CH:28]([CH2:3][O:4][C:5]3[CH:1]=[CH:2][CH:8]=[CH:7][CH:47]=3)[CH:27]([CH2:33][N:34]3[CH2:39][CH2:38][CH:37]([C:40]4[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=4)[CH2:36][CH2:35]3)[CH2:26]2)=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 70153550HCID 70153550, compound

Product 1

HCID 18723505HCID 18723505, compound

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

A solution of 0.062 g (0.14 mmol) of Ph3Bi (Aldrich) in 1 mL of CH2Cl2 and 0.65 mL of THF at rt was added 0.027 mL (0.18 mmol) of trifluoroacetic acid and the reaction mixture was stirred for 10 min. This solution was added to a solution of 0.046 g (0.1 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-hydroxyethylpyrrolidine in 1 mL of CH2Cl2. To this reaction mixture was added 0.0083 g (0.046 mmol) of Cu(OAc)2 and the reaction mixture was stirred at 40° C. for 72 h. The reaction mixture was filtered through a thin pad of silica (acetone:hexanes, 1:2) and the filtrate was concentrated. The residue was purified by chromatography (silica, Waters RCM 25×100 with (0.1% iPr2NH in methyl tbutyl ether):hexane=2.25:7.0) to give the title compound. 1H NMR (CDCl3) δ (key peaks) 7.88-7.92 (m, 3H), 7.47-7.56 (m, 4H), 7.23-7.34 (m, 2H), 7.07-7.18 (m, 2H), 6,92-7.01 (m, 4H), 6.80 (d, 1H, J=7.5 Hz), 5.12 (S, 2H). Mass Spectrum (ESI) m/e=523 (M+1).

Workup

  1. stirringthe reaction mixture was stirred at 40° C. for 72 h
  2. filtrationThe reaction mixture was filtered through a thin pad of silica (acetone:hexanes, 1:2)
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography (silica, Waters RCM 25×100 with (0.1% iPr2NH in methyl tbutyl ether):hexane=2.25:7.0)

Sources & evidence

ORD record
ord-0e59d4fad8a84402a67f383d2c3074a6
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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