Potassium Carbonate → (S)-1-(3-Methoxy-4-nitro-phenyl)-piperidine-3-carboxylic acid

HRID 1262043Notes

Reaction equation

HRID 1262043 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([C:19]([OH:21])=[O:20])[CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([C:19]([OH:21])=[O:20])[CH2:14]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisoleHCID 6575389Nipecotic acid, S-(+)-

Product 1

HCID 66711435(S)-1-(3-Methoxy-4-nitro-phenyl)-piperidine-3-carboxylic acidYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1-(3-Methoxy-4-nitro-phenyl)-piperidine-3-carboxylic acid was prepared by reacting 4-fluoro-2-methoxy-1-nitro-benzene (342 mg, 2.0 mmol) with (S)-Piperidine-3-carboxylic acid (258 mg, 2.0 mmol) at 80° C. in DMF using K2CO3 (608 mg, 2.20 mmol) as a base scavenger. After 16 h the reaction was concentrated under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous phase was acidified with 1N HCl to pH 4-5. The resulting yellow solid was filtered, rinsed with water, and air dried overnight to yield 352 mg (63%) of (S)-1-(3-Methoxy-4-nitro-phenyl)-piperidine-3-carboxylic acid as a yellow solid. LC/MS (E/I+) 281.08 (M+H).

Workup

  1. custom(S)-1-(3-Methoxy-4-nitro-phenyl)-piperidine-3-carboxylic acid was prepared
  2. customat 80° C.
  3. concentrationAfter 16 h the reaction was concentrated under reduced pressure
  4. customthe residue was partitioned between EtOAc and water
  5. filtrationThe resulting yellow solid was filtered
  6. washrinsed with water, and air
  7. customdried overnight

Sources & evidence

ORD record
ord-415a3fe39c9b4dca92fd6d50b4869751
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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