Pyrrolidine → HCID 57078170, compound

HRID 330181Notes

Reaction equation

[C:1]([CH:4]([CH3:31])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH3:17])[CH:10]=[C:9]2[CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=1[O:29][CH3:30])([OH:3])=O.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH3:30][O:29][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:19]=1[CH2:18][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([CH2:5][CH:4]([CH3:31])[C:1]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:3])[CH:7]=2)[N:11]([CH2:15][CH2:16][CH3:17])[CH:10]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 19870567HCID 19870567, compound

Product 1

HCID 57078170HCID 57078170, compound

Procedure

Using a similar procedure to that described in Example 49, part g, except starting from methyl 4-[5-(2-carboxypropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate, and using pyrrolidine instead of pentylamine, methyl 3-methoxy-4-[5-(2-methyl-3-pyrrolidino-3-oxopropyl)-1-propylindol-3-ylmethyl]benzoate was obtained (60%) as a colorless glass; partial NMR (250 MHz, DMSO-d6): 0.78(t, 3H, CH2CH3), 0.98(d, 3H, CH(CH3)), 1.4-1.8 (complex m, 6H), 2.6(m, 1H), 2.83(m, 4H), 3.3(complex m, 2H), 3.83(s, 3H, OCH3), 3.92(s, 3H, OCH3).

Sources & evidence

ORD record: ord-7d33d65fbbea4049bf28e58d113f3c4c
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04894386

Reaction notes

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