Benzyl 4-(2-(tert-butyldimethylsilyloxy)ethyl)piperazine-1-carboxylate → 1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)piperazine

HRID 2239528

Reaction equation

HRID 2239528 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[CH2:13][CH2:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58812409Benzyl 4-(2-(tert-butyldimethylsilyloxy)ethyl)piperazine-1-carboxylate

Product 1

HCID 582998241-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)piperazineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-(2-(tert-butyldimethylsilyloxy)ethyl)piperazine-1-carboxylate (Method 90, 2.1 g, 5.55 mmol) and Pd/C (0.059 g, 0.55 mmol) in methanol (30 mL) was stirred under H2 (g) for 24 hours. The reaction mixture was filtered through a pad of Celite and concentrated under reduced pressure to give 1.20 g, (88%) of a yellow oil. 1H NMR: CD3Cl 3.74 (t, 2H), 2.90 (m, 4H), 2.51 (m, 6H), 0.88 (s, 9H), 0.04 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-598620f990ba4d77a236db01de1f2e4d
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Linked notes

Loading…