2-Aminomethyl-1-ethylpyrrolidine → HCID 15870695, compound

HRID 582711Notes

Reaction equation

HRID 582711 reaction equation
[CH2:1]([O:11][C:12]1[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=O)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[NH2:23][CH2:24][CH:25]1[CH2:29][CH2:28][CH2:27][N:26]1[CH2:30][CH3:31]>>[CH2:30]([N:26]1[CH2:27][CH2:28][CH2:29][CH:25]1[CH2:24][NH:23][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH3:22])[C:12]=1[O:11][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4])[CH3:31]

Participants

3

Reactant 2

HCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 69853268HCID 69853268, compound

Product 1

HCID 15870695HCID 15870695, compoundYield 89%

Procedure

In a manner identical to Example 15, 2-geranyloxy-3-methoxybenzoic acid (1.52 g) was subjected to a condensation reaction with 2-aminomethyl-1-ethylpyrrolidine (0.7 ml), thereby yielding 1.84 g (89%) of the aimed compound. 1H-NMR (CDC3)δ: 8.38(1H, bs), 7.70(1H, dd, J=2.0 Hz, 7.8 Hz ), 7.12(11, dt, J=2.0 Hz, 7.8 Hz ), 7.00(7H, d, J=8.3 Hz), 5.53(1H, t, J=7.3 Hz), 5.07-5.02(1H, m,), 4.64(1H, d, J=7.3 Hz), 3.91(3H, s), 3.28-3.13(1H, m), 2.95-2.81(1H, m), 2.16-2.54(1H, m), 2.33-2.22(1H, m), 2.20-2.00(4H, m), 1.98-1.86(1H, m), 1.74(3H, s), 1.71(3H, s), 1.67(3H, s), 1.12(3H, t, J=7.3 Hz).

Sources & evidence

ORD record
ord-457cab6d354c4260a67d7f6bb3a04443
Source dataset
uspto-grants-1999_07
Patent number
US05925667

Reaction notes

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