(3S)-(-)-3-(Dimethylamino)pyrrolidine → (3S)-N,N-dimethyl-1-{4-[(1-methyl-1H-indol-3-yl)methyl]benzoyl}pyrrolidin-3-amine

HRID 1163097Notes

Reaction equation

HRID 1163097 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=2)=[CH:3]1.[CH3:22][N:23]([CH3:29])[C@H:24]1[CH2:28][CH2:27][NH:26][CH2:25]1>>[CH3:22][N:23]([CH3:29])[C@H:24]1[CH2:28][CH2:27][N:26]([C:16](=[O:17])[C:15]2[CH:20]=[CH:21][C:12]([CH2:11][C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[CH:13][CH:14]=2)[CH2:25]1

Participants

3

Reactant 2

HCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 58970761methyl 4-((1-methyl-1H-indol-3-yl)methyl)benzoate

Product 1

HCID 25031336(3S)-N,N-dimethyl-1-{4-[(1-methyl-1H-indol-3-yl)methyl]benzoyl}pyrrolidin-3-amine

Procedure

Using essentially the same procedure described in Example 228 and employing methyl 4-((1-methyl-1H-indol-3-yl)methyl)benzoate and (S)—N,N-dimethylpyrrolidin-3-amine as starting materials, the title compound is obtained as a white solid, mp 101-105° C., identified by H1 NMR and mass spectral analyses. MS (ES) m/z 362.2; MS (ES) m/z 723.4.

Sources & evidence

ORD record
ord-33ff6a40c6f2428a8c74a15dba0af196
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

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