(S)-4-Benzyl-2-(2-hydroxyethyl)piperazine-1-carboxylic acid tert-butyl ester → (S)-tert-butyl 2-(2-hydroxyethyl)piperazine-1-carboxylate

HRID 1598459Notes

Reaction equation

HRID 1598459 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:10]([CH2:21][CH2:22][OH:23])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[CH2:21][CH2:22][OH:23])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 15406045(S)-4-Benzyl-2-(2-hydroxyethyl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 12046236(S)-tert-butyl 2-(2-hydroxyethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Benzyl-1-tert-butoxycarbonyl-2(S)-(2-hydroxyethyl)piperazine (7.0 g, 21.8 mmol) was hydrogenated at 60 psi in methanol (80 mL) in the presence of 10% Pd/C (1.56 g) according to the procedure described in Example 2, Step C. The title compound was obtained as an oil (4.43 g). NMR (CD3OD, 300 MHz) δ 4.17 (1H, m), 3.80 (1H, d, J=4 Hz), 3.54 (2H, t, J=7Hz), 2.75-3.05 (4H, m), 2.58 (1H, dt, J=4, 13 Hz), 2.0 (1H, m), 1.8 (1H, m), 1.45 (9H, s).

Sources & evidence

ORD record
ord-ab643e18938a426ba1e3a109a76bd3f5
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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