Ethanol → 4-(((Benzyloxy)carbonyl)amino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

HRID 1664810Notes

Reaction equation

HRID 1664810 reaction equation
N[C:2]([C:4]1([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)=[O:3].C([OH:30])C>[Pd]>[CH2:21]([O:20][C:18]([NH:17][C:4]1([C:2]([OH:30])=[O:3])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:6][CH2:5]1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 10714606tert-Butyl 4-(((benzyloxy)carbonyl)amino)-4-carbamoylpiperidine-1-carboxylate

Product 1

HCID 27566404-(((Benzyloxy)carbonyl)amino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Palladium (10% on carbon; 210 mg) was added to a solution of tert-butyl 4-(aminocarbonyl)-4-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate (0.43 g, 1.14 mmol) in ethanol (20 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 18 h, the mixture was filtered and concentrated to give the title compound (290 mg).

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (1 atm)
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-89fadd86f4d449e59f14afb14ccc9107
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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