Benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamate → 1,1-Dimethylethyl N-[1-(2-aminoethyl)-4-piperidinyl]carbamate

HRID 656958Notes

Reaction equation

HRID 656958 reaction equation
C1(COC([NH:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]2)=O)C=CC=CC=1>C(O)C.[Pd]>[NH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 22989976Benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamate

Product 1

HCID 235626471,1-Dimethylethyl N-[1-(2-aminoethyl)-4-piperidinyl]carbamateYield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1,1-dimethylethyl {1-[2-({[(phenylmethyl)oxy]carbonyl}amino)ethyl]-4-piperidinyl}carbamate (8.2 g, 21.8 mmol) in ethanol (500 ml) was hydrogenated overnight over 10% palladium on charcoal (50% dispersion with water, 4.0 g). The mixture was filtered, evaporated, and azeotroped with chloroform to afford the title intermediate (5.4 g, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customazeotroped with chloroform

Sources & evidence

ORD record
ord-7c39fd70e4614128b5e93581d7484dd1
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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