4-Benzyl-1-tert-butoxycarbonyl-2(S)-(2-methoxyethyl)piperazine → (S)-Tert-butyl 2-(2-methoxyethyl)piperazine-1-carboxylate

HRID 1598449Notes

Reaction equation

HRID 1598449 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][O:23][CH3:24])[CH2:9]1)C1C=CC=CC=1>[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][O:23][CH3:24])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

3

Reactant 1

HCID 154060464-Benzyl-1-tert-butoxycarbonyl-2(S)-(2-methoxyethyl)piperazine

Product 1

HCID 15406047(S)-Tert-butyl 2-(2-methoxyethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound was prepared according to the procedure described in Example 2, Step C, except using 4-benzyl-1-tert-butoxycarbonyl-2(S)-(2-methoxyethyl)piperazine (0.280 g, 0.83 mmol) and 10% palladium on carbon (80 mg). The title compound was obtained as an oil (179 mg). NMR (CD3OD, 300 MHz) δ 4.17 (1H, m), 3.81 (1H, dd, J=3, 13 Hz), 3.38 (2H, t, J=6 Hz), 2.82-3.02 (2H, m), 2.77 (2H, ABq, J=4, 13 Hz), 2.59 (1H, dt, J=4, 7 Hz), 2.04 (1H, m), 1.84 (1H, m), 1.46 (9H, s).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c1d9a9bdfe8d42d9b633ec544cf0328a
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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