1-Phenylcyclobutylamine → 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)-N-(1-phenylcyclobutyl)acetamide

HRID 1667073Notes

Reaction equation

HRID 1667073 reaction equation
[C:1]1([C:7]2([NH2:11])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:12]=[C:13]1[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]1[CH2:30][C:31](O)=[O:32].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[O:12]=[C:13]1[C:17]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]1[CH2:30][C:31]([NH:11][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:10][CH2:9][CH2:8]1)=[O:32]

Participants

5

Reactant 3

HCID 1522141-PhenylcyclobutylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 452755992-(2-oxo-3,3-diphenylpyrrolidin-1-yl)-N-(1-phenylcyclobutyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-phenylcyclobutanamine (0.030 g, 0.204 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (0.055 g, 0.185 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.036 g, 0.185 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.31-7.39 (m, 7H), 7.17-7.31 (m, 8H), 6.42-6.44 (br s, 1H), 3.94 (s, 2H), 3.46 (t, J=6.5 Hz, 2H), 2.79 (t, J=6.5 Hz, 2H), 2.42-2.52 (m, 2H), 2.19-2.30 (m, 2H), 1.71-1.95 (m, 2H); MS (ESI−) m/z 423 (M−H)−.

Workup

  1. washthe title compound was eluted
  2. customover 20 minutes

Sources & evidence

ORD record
ord-1ad0cf9b371c498084e152e5d001599f
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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