Formaldehyde → Ethyl 2-(1-methyl-3-(3-(4-octylphenyl)ureido)pyrrolidin-3-yl)acetate

HRID 1192903Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of ethyl 2-(3-(3-(4-octylphenyl)ureido)pyrrolidin-3-yl)acetate (84 mg, 0.2 mmol) in formic acid (2 mL) was added formalin (15 μL, 0.16 mL). The solution was heated to 110° C. for 2 h. The mixture was concentrated and dissolved into CH2Cl2 (25 mL) and washed with sat. bicarbonate (2×5 mL), H2O (5 mL), dried over MgSO4 and concentrated to dryness to give the title compound as a brown oil (29 mg, 35%) MS ESI 418.4 [M+H]+, calcd for [C24H39N3O3+H] 418.30.

Workup

concentrationThe mixture was concentrated
dissolutiondissolved into CH2Cl2 (25 mL)
washwashed with sat. bicarbonate (2×5 mL), H2O (5 mL)
dry with materialdried over MgSO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-9e1429816bcd48c3bec0ec47fa003b9f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680282B2

Reaction notes

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