HCID 68497982, compound → HCID 68493404, compound

HRID 1944201Notes

Reaction equation

HRID 1944201 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[CH2:6][N:7]1[CH:16]([CH3:17])[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:26][CH3:27])=[C:12]([O:18]CC3C=CC=CC=3)[CH:13]=2)[CH2:8]1>C1COCC1.CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[CH2:6][N:7]1[CH:16]([CH3:17])[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:26][CH3:27])=[C:12]([OH:18])[CH:13]=2)[CH2:8]1

Participants

5

Reactant 1

HCID 68497982HCID 68497982, compound

Product 1

HCID 68493404HCID 68493404, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 214 (330 mg, 0.82 mmol) in THF (6 mL) and EtOH (6 mL) was treated with 10% Pd/C (33 mg) and stirred under an atmosphere of hydrogen. The reaction was monitored by TLC. Upon completion, the resultant suspension was filtered through celite, washed with ethyl acetate and then evaporated under reduced pressure. Purification (personal flashmaster: 20 g, hex:EtOAc; 2:1) afforded the title compound (118 mg, 46%) as a pale yellow solid. mp=100-105° C. 1H NMR (270 MHz; CDCl3) 1.12 (3H, d, J=6.7 Hz, CH3CH), 2.49 (1H, dd, J=16.1, 5.8 Hz, CHH), 2.89 (1H, dd, J=16.1, 4.8 Hz, CHH), 3.01-3.12 (1H, m, CHCH3), 3.48-3.74 (4H, m, 2×CH2), 3.78 (3H, s, OCH3), 3.79 (3H, s, OCH3), 5.42 (1H, s, OH), 6.42 (1H, s, CH), 6.63 (1H, s, CH), 6.77-6.81 (1H, m, CH), 6.93-6.96 (2H, m, 2×CH), 7.21 (1H, d, J=8.2 Hz, CH). 13C NMR (67.5 MHz; CDCl3) 15.39 (CH3), 34.68 (CH2), 51.43 (CH2), 52.30 (CH), 55.31 (OCH3), 55.99 (OCH3), 57.07 (CH2), 108.73 (CH), 112.54 (CH), 114.35 (CH), 114.54 (CH), 121.36 (CH), 125.48 (C), 126.56 (C), 129.29 (CH), 141.20 (C), 144.04 (C), 144.92 (C), 159.75 (C). LC/MS (ES+) tr=2.43 min, m/z 314.18 (M++H). HRMS (ES+) calcd. for C19H24NO3 314.1751, found 314.1748.

Workup

  1. filtrationUpon completion, the resultant suspension was filtered through celite
  2. washwashed with ethyl acetate
  3. customevaporated under reduced pressure
  4. customPurification (personal flashmaster: 20 g, hex:EtOAc; 2:1)

Sources & evidence

ORD record
ord-1743a12987d64239811dc253d87ee603
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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