(2S,4S)-Benzyl 2-(6-fluoropyridin-3-ylcarbamoyl)-4-methoxypyrrolidine-1-carboxylate → (2S,4S)-N-(6-fluoropyridin-3-yl)-4-methoxypyrrolidine-2-carboxamide

HRID 1961385Notes

Reaction equation

HRID 1961385 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C@@H:11]2[CH2:15][C@H:14]([O:16][CH3:17])[CH2:13][N:12]2C(OCC2C=CC=CC=2)=O)=[O:10])=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[F:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C@@H:11]2[CH2:15][C@H:14]([O:16][CH3:17])[CH2:13][NH:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 59436347(2S,4S)-Benzyl 2-(6-fluoropyridin-3-ylcarbamoyl)-4-methoxypyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59436349(2S,4S)-N-(6-fluoropyridin-3-yl)-4-methoxypyrrolidine-2-carboxamideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred suspension of palladium on carbon (10%, 80 mg) in methanol (100 mL) was added a solution of (2S,4S)-benzyl 4-methoxy-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate 62A (400 mg, 1.12 mmol) in methanol (100 mL) under nitrogen. The suspension was hydrogenated with a hydrogen balloon atmosphere overnight. The resulting suspension was filtered through a pad of celite and washed with methanol. Concentration of the filtrate gave the product as an oil (250 mg, 100%) which was used without purification in the next step. LC/MS [M+H]+: 240; Ret time (Method F): 0.91 min.

Workup

  1. filtrationThe resulting suspension was filtered through a pad of celite
  2. washwashed with methanol

Sources & evidence

ORD record
ord-8894165ab756431d80629e4d47860269
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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