3,3-Diphenylpyrrolidine → HCID 45274933, compound

HRID 1667215Notes

Reaction equation

HRID 1667215 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]([OH:17])=O)[C:9]2=[O:18])=[CH:4][CH:3]=1.[C:26]1([C:32]2([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:36][CH2:35][NH:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[C:26]1([C:32]2([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:36][CH2:35][N:34]([C:15](=[O:17])[CH2:14][N:10]3[CH2:11][CH2:12][CH2:13][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)([C:19]4[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=4)[C:9]3=[O:18])[CH2:33]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 4182423,3-DiphenylpyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673591112-(3,3-Bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetic acid

Product 1

HCID 45274933HCID 45274933, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3,3-bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetic acid (Example 90D, 0.345 g, 1.0 mmol) in dichloromethane (20 mL) under nitrogen was added 3,3-diphenylpyrrolidine (Example 17A, 0.223 g, 1.0 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.383 g, 2.0 mmol) and N,N-dimethylpyridin-4-amine (0.012 g, 0.10 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, 200 mL). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (Analogix®, Burlington, Wis.) eluting with ethyl acetate/hexane (1:1) gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.32-7.15 (m, 14H), 6.98 (t, J=8.7, 4H), 4.22 (d, J=3.0, 2H), 4.09 (d, J=3.5, 2H), 3.62-3.45 (m, 4H), 2.67-2.49 (m, 4H), 1.84 (d, J=5.6, 2H); MS (DCI) m/z 551.2 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was partitioned in ethyl acetate/water (8:2, 200 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography (Analogix®, Burlington, Wis.) eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-df7b78824c0b41c0807a4e8e2a2174e7
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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