Potassium Hydroxide → 1-(1-Naphthoyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidine

HRID 279219Notes

Reaction equation

HRID 279219 reaction equation
[CH2:1]([N:4]1[CH2:8][CH:7]([CH:9]2[CH2:11][CH2:10]2)[CH:6]([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH2:5]1)[CH:2]=[CH2:3].[OH-:26].[K+]>CO.O>[C:2]1([C:1]([N:4]2[CH2:8][C@@H:7]([CH:9]3[CH2:10][CH2:11]3)[C@H:6]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)[CH2:5]2)=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:15][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 226244721-Allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

Product 1

HCID 187135061-(1-Naphthoyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidineYield 41.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 6 g (48 mmol) of methyl-3-(cyclopropyl)acrylate (Example 1, Step 3) and 5.7 g (100 mmol) of KOH in 25 mL of MeOH and 2 mL of H2O was stirred at 40° C. for 2 h. The reaction mixture was concentrated. Addition of 2N HCl to the residue resulted in its precipitation as a white solid. The solid was collected by filtration and was washed with H2O and dried to give 4.5 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionAddition of 2N HCl to the residue
  3. customresulted in its precipitation as a white solid
  4. filtrationThe solid was collected by filtration
  5. washwas washed with H2O
  6. customdried

Sources & evidence

ORD record
ord-79a69d0fc399440cbea134eec6bbf9e8
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

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