Formaldehyde → HCID 66865240, compound

HRID 1192909Notes

Reaction equation

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

Participants

Reactant 2

HCID 712Formaldehyde

HCID 66865770HCID 66865770, compound

Product 1

HCID 66865240HCID 66865240, compoundYield 75%

Procedure

According to the method described in example 17c, ethyl 2-(3-(4-decylbenzamido)-pyrrolidin-3-yl)acetate was reacted with formalin to give the title compound as a yellow oil (58 mg, 75%). 1H NMR (400 MHz, CDCl3) δ 7.67 (d, 2H, J=7.9 Hz), 7.21 (d, 2H, J=8.1 Hz), 6.70 (s, 1H), 4.10 (q, 2H, J=7.1 Hz), 3.17-2.82 (m, 4H), 2.77-2.67 (m, 2H), 2.63 (t, 2H, J=7.8 Hz), 2.37 (s, 3H), 2.35-2.30 (m, 1H), 1.64-1.55 (m, 2H), 1.36-1.24 (m, 14H), 1.20 (t, 3H, J=7.3 Hz), 0.89 (t, 311, J=6.6 Hz); MS ESI 431.4[M+H]+, calcd for [C26H42N2O3+H] 431.32.

Sources & evidence

ORD record: ord-3a0709d430a0499dbca56fa56840408c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680282B2

Reaction notes

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