HCID 11109638, compound → HCID 86702795, compound

HRID 1425913Notes

Reaction equation

HRID 1425913 reaction equation
[C@@H:1]12[N:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([CH:5]=[CH:6]1)[C:3]([C:15]([O:17][CH3:18])=[O:16])=[C:2]2[C:19]([O:21][CH3:22])=[O:20]>CO.O=[Pt]=O>[C@@H:4]12[N:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:1]([CH2:6][CH2:5]1)[CH:2]([C:19]([O:21][CH3:22])=[O:20])[CH:3]2[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 1

HCID 11109638HCID 11109638, compound

Product 1

HCID 86702795HCID 86702795, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

(1R,4S)-7-tert-butyl 2,3-dimethyl 7-azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylate (XLVII) (3.41 g, 11.04 mmol) was dissolved in MeOH (50 mL) under an argon atmosphere. Adams' catalyst was added and the reaction was flushed with hydrogen. The mixture was stirred under hydrogen overnight at room temperature. The catalyst was filtered off and the solvent was removed in vacuo to give a yellow oil. The oily residue was crystallized from hot heptane to give (1R,4S)-7-tert-butyl 2,3-dimethyl 7-azabicyclo[2.2.1]heptane-2,3,7-tricarboxylate (XLVIII) as a white solid (3.28 g, 10.49 mmol, 95% yield). 1H NMR (CDCl3) (two isomers in a 3/1 ratio) δ ppm [1.40 (s, 2nd isomer), 1.44 (s, 2nd isomer), 9H], 1.60-2.00 (m, 4H), [3.66 (s, 1st isomer), 3.71 (s, 2nd isomer), 6H], [4.37 (brs, 1st isomer), 4.51 (brs, 2nd isomer), 2H]; ESIMS found for C15H23NO6 m/z 336 (M+Na).

Workup

  1. customthe reaction was flushed with hydrogen
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was removed in vacuo
  4. customto give a yellow oil
  5. customThe oily residue was crystallized from hot heptane

Sources & evidence

ORD record
ord-0038311880724407a6ef0dce51d17b5b
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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