Pyridine → 1-(1-Naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

HRID 279217Notes

Reaction equation

HRID 279217 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]3[CH:19]([CH:20]4[CH2:22][CH2:21]4)[CH2:18][NH:17][CH2:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:29]1([C:39](Cl)=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:29]1([C:39]([N:17]2[CH2:18][CH:19]([CH:20]3[CH2:21][CH2:22]3)[CH:15]([CH2:14][N:11]3[CH2:12][CH2:13][CH:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:9][CH2:10]3)[CH2:16]2)=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 701461-Naphthalenecarbonyl chlorideHCID 226244713-(RS)-(4-(4-Fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

Product 1

HCID 98253091-(1-Naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.02 g (0.067 mmol) of 3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine and 0.12 mL of pyridine in 2 mL of CH2Cl2 at rt was added 0.19 g (1 mmol) of 1-naphthoyl chloride and the reaction mixture was stirred for 1 h. The reaction mixture was partitioned between ethyl acetate and sat'd NaHCO3 solution. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (HPLC Waters Nova-Pak 8×10 RCM 25-40% MeOH in H2O 0.5%TFA) to give the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and sat'd NaHCO3 solution
  2. dry with materialThe organic fraction was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chomatography (HPLC Waters Nova-Pak 8×10 RCM 25-40% MeOH in H2O 0.5%TFA)

Sources & evidence

ORD record
ord-3946c66a31524ad98b9860d797017ce8
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

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