3,3-Diphenylpyrrolidine → HCID 45275697, compound

HRID 1667080Notes

Reaction equation

HRID 1667080 reaction equation
[C:1]1([C:7]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:18]=[C:19]1[C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:21][N:20]1[CH2:36][C:37](O)=[O:38].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[C:1]1([C:7]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:11][CH2:10][N:9]([C:37](=[O:38])[CH2:36][N:20]3[CH2:21][CH2:22][C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:19]3=[O:18])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 4182423,3-DiphenylpyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45275697HCID 45275697, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,3-diphenylpyrrolidine (Example 17A, 0.22 g, 1.00 mmol) in dichloromethane (20 mL) under nitrogen was added 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.30 g, 1.00 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.38 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (0.61 mg, 0.005 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate/water (8:2, 400 mL). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (1:1) gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.40 (m, 20H), 4.14-4.25 (m, 2H), 4.09-4.12 (m, 2H), 3.38-3.61 (m, 4H), 2.75-2.87 (m, 2H), 2.49-2.63 (m, 2H); MS (DCI+) m/z 501 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was partitioned in ethyl acetate/water (8:2, 400 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-04250c9b36164ae99cbeefbed5ce8a6e
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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