Ethyl (2E)-4-oxo-2-butenoate → Ethyl 2-((3S,4S)-4-(4-acetylphenyl)-1-(4-methoxyphenylsulfonyl)-2-oxo-1,2,3,4-tetrahydro-pyridin-3-yl)acetate

HRID 1886846Notes

Reaction equation

HRID 1886846 reaction equation
[O:1]=[CH:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:21]=[CH:22]/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][CH:26]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[C:31]([C:28]1[CH:27]=[CH:26][C:25]([C@H:24]2[CH:23]=[CH:22][N:21]([S:18]([C:15]3[CH:14]=[CH:13][C:12]([O:11][CH3:10])=[CH:17][CH:16]=3)(=[O:20])=[O:19])[C:2](=[O:1])[C@H:3]2[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:30][CH:29]=1)(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 7019541Ethyl (2E)-4-oxo-2-butenoateHCID 68486302trans-N-(4-methoxybenzenesulfonyl)-1-(4-(3-iminoprop-1-enyl)phenyl)ethanone

Product 1

HCID 59445886Ethyl 2-((3S,4S)-4-(4-acetylphenyl)-1-(4-methoxyphenylsulfonyl)-2-oxo-1,2,3,4-tetrahydro-pyridin-3-yl)acetateYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared according to the general procedure from ethyl trans-4-oxo-2-butenoate and trans-N-(4-methoxybenzenesulfonyl)-1-(4-(3-iminoprop-1-enyl)phenyl)ethanone using 10 mol % 9 as the catalyst in 55% yield as a yellow oil. [α]D20 (c 1.22, CHCl3)=+168.2; 1H NMR (400 MHz, CDCl3) δ 8.04 (dd, 2H, J=6.9, 2.1 Hz), 7.59 (dd, 2H, J=6.5, 1.9 Hz), 7.19 (d, 1H, J=8.0 Hz), 7.07 (dd, 2H, J=6.9, 2.1 Hz), 6.69 (dd, 2H, J=6.6, 1.7 Hz), 5.59 (dd, 1H, J=8.0, 6.6 Hz), 4.14-4.11 (m, 2H), 3.95 (s, 3H), 3.74 (t, 1H, J=6.9 Hz), 3.58-3.53 (m, 1H), 2.58 (dd, 1H, J=17.4, 6.0 Hz), 2.52 (s, 3H), 1.90 (dd, 1H, J=17.4, 7.8 Hz), 1.22 (t, 3H, J=7.2 Hz); 13C NMR (100 MHz, CDCl3) δ 197.5, 171.5, 168.6, 164.5, 142.3, 136.6, 131.4, 128.9, 128.2, 125.3, 114.3, 112.7, 94.6, 61.1, 56.1, 43.9, 41.7, 31.4, 26.7, 14.3; IR (thin film) ν 3020, 2983, 2842, 1723, 1682, 1594, 1497, 1363, 1267, 1167, 1091, 1024 cm−1; HRMS (ESI) calcd for C24H25NO7S [M+Na]+ 494.1243, found 494.1265; >99% ee (3S,4S)-isomer as determined by HPLC(OD-H, 4:1 hexanes/i-PrOH), tr (3S,4S)=28.6 min, tr (3R,4R)=35.1 min.

Workup

  1. customPrepared
  2. customtr (3S,4S)=28.6 min, tr (3R,4R)=35.1 min.

Sources & evidence

ORD record
ord-c5416350f2984ac4be58ea8525d6b299
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

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