Benzyl 4-({(3S)-3-[(tert-Butoxycarbonyl)amino]pyrrolidin-1-yl}carbonyl)piperidine-1-carboxylate → tert-butyl [(3S)-1-(piperidin-4-ylcarbonyl)pyrrolidin-3-yl]carbamate

HRID 2367041Notes

Reaction equation

HRID 2367041 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]([CH:16]2[CH2:21][CH2:20][N:19](C(OCC3C=CC=CC=3)=O)[CH2:18][CH2:17]2)=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[NH:19]1[CH2:18][CH2:17][CH:16]([C:14]([N:11]2[CH2:12][CH2:13][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10]2)=[O:15])[CH2:21][CH2:20]1

Participants

4

Reactant 1

HCID 57803376Benzyl 4-({(3S)-3-[(tert-Butoxycarbonyl)amino]pyrrolidin-1-yl}carbonyl)piperidine-1-carboxylate

Product 1

HCID 57803247tert-butyl [(3S)-1-(piperidin-4-ylcarbonyl)pyrrolidin-3-yl]carbamateYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-({(3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidin-1-yl}carbonyl)piperidine-1-carboxylate (7.5 g, 17 mmol) and palladium on carbon (800 mg, 8 mmol) in methanol (100 mL) was shaken under hydrogen at 50 psi overnight. The mixture was filtered through celite and the filtrate was concentrated to give 5.1 g of product as a white solid. MS (M+H) 298.2.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-feddd9c46df841ebaaba797f26891478
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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