benzyl (3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]-1,3'-bipyrrolidine-1'-carboxylate → N-{2-[(3R)-1,3'-bipyrrolidin-3-ylamino]-2-oxoethyl}-3-(trifluoromethyl)benzamide

HRID 562580Notes

Reaction equation

HRID 562580 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:22][CH2:21][N:20](C(OCC3C=CC=CC=3)=O)[CH2:19]2)[CH2:14]1)=[O:11])=[O:7].[H][H]>CO.[Pd]>[N:15]1([CH:18]2[CH2:22][CH2:21][NH:20][CH2:19]2)[CH2:16][CH2:17][C@@H:13]([NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:33]=[CH:34][CH:35]=[C:3]([C:2]([F:37])([F:36])[F:1])[CH:4]=2)[CH2:14]1

Participants

5

Reactant 2

HCID 16061463benzyl (3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]-1,3'-bipyrrolidine-1'-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67006850N-{2-[(3R)-1,3'-bipyrrolidin-3-ylamino]-2-oxoethyl}-3-(trifluoromethyl)benzamideYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a round-bottom flask, a slurry of benzyl (3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]-1,3′-bipyrrolidine-1′-carboxylate (0.765 g, 1.48 mmol) and Palladium (10%) on Carbon (0.200 g) in methanol (10 mL) was purged with hydrogen gas for 2 min.; the reaction was then subjected to 1 atm of hydrogen gas for 3 h. The flask was purged with Argon, then the mixture was filtered and concentrated to afford N-{2-[(3R)-1,3′-bipyrrolidin-3-ylamino]-2-oxoethyl}-3-(trifluoromethyl)benzamide (0.551 g, 97%) as an off-white solid. 1H-NMR (CDCl3) δ: 1.32-1.53 (m, 2H), 1.52-2.04 (m, 6H), 2.15-2.40 (m, 2H), 2.40-2.70 (m, 3H), 2.80-3.00 (m, 3H), 4.00-4.20 (m, 2H), 4.42 (bs, 1H), 6.77 (m, 1H), 7.40-7.55 (m, 1H), 7.53 (t, J=7.8 Hz, 1H), 7.73 (d, J=7.2 Hz, 1H), 7.98 (d, J=7.5 Hz, 1H), 8.08 (s, 1H). MS m/z: 399 (M+1).

Workup

  1. customThe flask was purged with Argon
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c215b38d8d7443998498d63b00435550
Source dataset
uspto-grants-2011_11
Patent number
US08067415B2

Reaction notes

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