HCID 58237947, compound → HCID 44194570, compound

HRID 1192931Notes

Reaction equation

HRID 1192931 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH2:20][CH:21]=[CH2:22])[CH2:14][C:15]([O:17]CC)=O)[CH3:9])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:20]([C@:13]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:12][CH2:11][N:10]([C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH3:9])[C:15](=[O:17])[CH2:14]1)[CH:21]=[CH2:22]

Participants

3

Reactant 1

HCID 58237947HCID 58237947, compound

Product 1

HCID 44194570HCID 44194570, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 3-(2-((S)-1-(4-bromophenyl)ethylamino)ethyl)-3-phenylhex-5-enoate (4.6 g, 9.1 mmol) in anhydrous toluene (80 mL) was heated to reflux for 2 days. The reaction was concentrated to give the crude (S)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-phenylpiperidin-2-one. The residue was purified by column chromatography to give the final product (1.2 g, 33%). 1H NMR (CDCl3): δ 1.13 (m, 3H), 1.76 (m, 1H), 1.97 (m, 1H), 2.24 (m, 1H), 2.43 (m, 2H), 2.57 (m, 2H), 2.94 (m, 1H), 4.89 (m, 2H), 5.35 (m, 1H), 6.01 (m, 1H), 7.03 (m, 2H), 7.21 (m, 3H), 7.30 (m, 2H), 7.42 (m, 2H).

Workup

  1. temperatureto reflux for 2 days
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-cff04eb870024d5b9ee4bcd13544e4ba
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

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