HCID 22046657, compound → HCID 22046689, compound

HRID 1826134Notes

Reaction equation

HRID 1826134 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:25])[N:10]3[CH2:24][CH2:23][CH2:22][CH:11]3[CH2:12][N:13](C(OCC(Cl)(Cl)Cl)=O)[C:7]=2[CH:6]=[C:5]([O:26][CH3:27])[C:4]=1[O:28][CH3:29]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:25])[N:10]3[CH2:24][CH2:23][CH2:22][CH:11]3[CH2:12][NH:13][C:7]=2[CH:6]=[C:5]([O:26][CH3:27])[C:4]=1[O:28][CH3:29]

Participants

4

Reactant 1

HCID 22046657HCID 22046657, compound

Product 1

HCID 22046689HCID 22046689, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Cd/Pb couple (2.57 g, 20.6 mmol Cd) was added to a stirred solution of 112 (2.00 g, 4.1 mmol) in THF (20 mL) and 1N NH4OAc buffer (20 mL) and left at room temperature for 4 h. The reaction mixture was diluted with EtOAc (200 mL) and washed with water (2×100 mL). The organic layer was washed with brine (2×100 mL) and dried (MgSO4). The solvent was removed in vacuo to give 113 (0.76 g, 64%) as a yellow glass: Rf=0.1 (silica, EtOAc); [α]20.7D=+505° (c=0.1, DCM); IR (neat) cm−1 3339, 2976, 2939, 1614, 1455, 1428, 1392, 1359, 1275, 1245, 1203, 1113, 1052, 1035, 1000, 926, 804, 751, 665; 1H NMR (270 MHz, CDCl3) δ (1H, d, J=4.39 Hz), 6.61 (1H, s), 6.14 (1H, d, J=8.24 Hz), 4.36 (1H, d, J=8.79 Hz), 4.01 (3H, s), 3.98 (3H, s), 3.84 (3H, s), 3.48-3.46 (2H, m) 2.26-2.23 (2H, m), 2.16-1.93 (2H, m); HRMS (FAB) calcd for C15H18N2O4 (M+1) 290.1266, found 290.1208.

Workup

  1. washwashed with water (2×100 mL)
  2. washThe organic layer was washed with brine (2×100 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-692cf6a5919442f0ab54ae0f9d771bcd
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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