1-Methylpiperazine → (4-Methyl-piperazin-1-yl)-pyrrolidin-2-yl-methanone

HRID 1373291Notes

Reaction equation

[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:3]([CH:2]2[CH2:6][CH2:7][CH2:8][NH:1]2)=[O:5])[CH2:12][CH2:11]1

Participants

Reactant 2

HCID 531671-Methylpiperazine

HCID 145742L-Proline

Product 1

HCID 14084856(4-Methyl-piperazin-1-yl)-pyrrolidin-2-yl-methanone

Procedure

Using analogous procedures to those described in Note [33] immediately above, 1-tert-butoxycarbonyl)-L-proline was reacted with 1-methylpiperazine to give (2S)-1-tert-butoxycarbonyl)-2-(4-methylpiperazin-1-ylcarbonyl)pyrrolidine which was deprotected and reacted with 2-bromoethanol. There was thus obtained the required starting material; NMR Spectrum: (CDCl3) 1.7–2.05 (m, 4H), 2.1–2.25 (m, 1H), 2.32 (s, 3H), 2.35–2.5 (m, 4H), 2.6–2.7 (m, 1H), 2.8–2.9 (m, 1H), 3.3–3.7 (m, 8H), 4.15 (br s, 1H); Mass Spectrum: M+H+ 242.

Sources & evidence

ORD record: ord-b57c9fa0806041a6bbdcc451131731db
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160891B2

Reaction notes

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