1,1-Dimethylethyl (2S)-2-(phenylmethyl)-1-piperazinecarboxylate → (S)-3-benzyl-1-(4-methoxy-3-((S)-1-methylpyrrolidin-3-yloxy)phenyl)piperazine

HRID 1423111Notes

Reaction equation

HRID 1423111 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([CH:14]=1)[O:7][C@H:8]1[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9]1.C(OC([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][C@@H:25]1[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=O)(C)(C)C>>[CH2:30]([C@@H:25]1[NH:24][CH2:29][CH2:28][N:27]([C:2]2[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([O:7][C@H:8]3[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9]3)[CH:14]=2)[CH2:26]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 177504411,1-Dimethylethyl (2S)-2-(phenylmethyl)-1-piperazinecarboxylateHCID 66824451(3S)-3-(5-Bromo-2-methoxyphenoxy)-1-methylpyrrolidine

Product 1

HCID 52918525(S)-3-benzyl-1-(4-methoxy-3-((S)-1-methylpyrrolidin-3-yloxy)phenyl)piperazine

Procedure

The title compound was prepared by the method outlined for Example 1 using (3S)-3-(5-Bromo-2-methoxyphenoxy)-1-methylpyrrolidine as the aryl halide and 2(S)-benzyl-piperazine-1-carboxylic acid tert-butyl ester as the amine component. The title compound was isolated as an orange oil. 1H NMR (MeOH-d4) 7.33-7.30 (m, 2H), 7.26-7.22 (m, 3H), 6.83 (d, J=9.2, 1H), 6.44 (m, 2H), 4.81 (m, 1H), 3.73 (s, 3H), 3.36-3.28 (m, 2H), 3.04 (m, 2H), 2.93-2.66 (m, 8H), 2.52-2.46 (m, 1H), 2.36 (s, 3H), 2.19 (m, 1H), 1.95 (m, 1H).

Workup

  1. customThe title compound was prepared by the method

Sources & evidence

ORD record
ord-1bfb02e5934e4c849d2f102a7b922b1f
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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