HCID 14835579, compound → HCID 23035271, compound

HRID 1709981Notes

Reaction equation

HRID 1709981 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[C:9](C(OCC)=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CCO.O=[Pt]=O>[CH2:1]([O:3][C:4]([N:6]1[C:12]2=[CH:13][CH:14]=[CH:15][CH2:16][C:11]2=[C:10]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 14835579HCID 14835579, compound

Product 1

HCID 23035271HCID 23035271, compoundYield 155.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 9 (5.5 g, 19 mmoles) in EtOH (55 ml) containing PtO2 (300 mg) was reduced (9 Atm, 25° C.) in a steel bomb for 10 hours. The catalyst was filtered and the solvent was evaporated to dryness. The residue was chromatographed [Silica gel: 120 g; eluent CHCH2Cl3 /EtOAc (95/5)] to give pure 11 (4.3 g, 80%) mp 60° C. (Calc. for C16H21NO4 : C 65.96; H 7.27; N 4.81 Found C 65.76; H 7.55; N 4.82) 1H NMR (CDCl3) δ=1.2 (6H, 2 overlapped t, J=7 Hz) 1.8-2.2 (2H, m) 2.3-2.7 (1H, m) 2.8-3.05 (2H, m) 3.2-3.7 (1H, m) 3.8-4.3 (5H, 2 overlapped q, J=7 Hz) 7.1 (4H, s). IR (CHCl3) 2980 (m) 2930 (m) 1725 (s) 1690 (s) 1610 (w) 1590 (w) 1490 (w) 1440 (w) 1410 (w) 1385 (w) 1310 (m). Mass spectrum m/z 291.

Workup

  1. custom(9 Atm, 25° C.)
  2. customfor 10 hours
  3. filtrationThe catalyst was filtered
  4. customthe solvent was evaporated to dryness
  5. customThe residue was chromatographed [Silica gel: 120 g; eluent CHCH2Cl3 /EtOAc (95/5)]

Sources & evidence

ORD record
ord-37f4961f2299444abaeb108e6992f8d5
Source dataset
uspto-grants-1990_08
Patent number
US04952573

Reaction notes

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