Acetic Acid → HCID 54299104, compound

HRID 1631855Notes

Reaction equation

HRID 1631855 reaction equation
C(OC([C@H]1[C@H]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])N1)=O)C.[NH:18]1[CH2:20][CH2:19]1.[C:21](O)(=[O:23])C.[CH:25](Cl)(Cl)Cl.[CH3:29][OH:30]>[Pd]>[CH2:29]([O:30][C:21](=[O:23])[C@H:20]([CH3:19])[NH:18][C:9]1[C:10]([CH3:17])=[CH:11][C:12]([CH3:16])=[CH:13][C:14]=1[CH3:15])[CH3:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 6212ChloroformHCID 86648063HCID 86648063, compound

Product 1

HCID 54299104HCID 54299104, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

9.9 g (42.42 mmol) of the aziridine ethyl (2R,3S)-3-mesityl-aziridine-2-carboxylate were dissolved in a high pressure reactor in 300 mL of methanol, and 990 mg of Pd/C and 10 mL of acetic acid (84.84 mmol) were added next. The system was purged with vacuum/nitrogen cycles and then the reactor was pressurized with 40 bar of hydrogen. The reaction mixture was maintained under stirring at room temperature for 48 hours. After this time, the catalyst was removed by means of celite filtration and the resulting solution was concentrated under reduced pressure. Compound (IIa) was obtained quantitatively in the form of a yellow solid. Mp 81-83° C. [α]D=−26.7 (c 1.00, CHCl3). IR (film): ν max 2918, 1742, 1612, 1483, 1225. 1H NMR (400 MHz, CDCl3) δ: 6.84 (s, 2H), 5.61 (b, 1H), 4.14 (m, 2H), 3.77 (dd, 1H, J=6.4 and 7.6 Hz), 3.08 (m, 2H), 2.94 (m, 2H), 2.31 (s, 6H), 2.25 (s, 3H), 1.18 (t, 3H, J=7 Hz) ppm. 13C NMR (100 MHz, CDCl3) δ178.9 (CO), 137.1 (C), 136.3 (C), 131.1 (C), 129.5 (CH), 129.5 (CH), 129.2 (C), 61.4 (CH2), 54.1 (CH), 34.6 (CH2), 24.9 (CH3), 21.0 (CH3), 19.8 (CH3), 14.2 (CH3) ppm. EM (ESI+) m/z: 236.2 [(M+H)+, 100%]. HRMS (ESI+): Calculated for C14H22NO2: 236.1645, 236.1637 found.

Workup

  1. customThe system was purged with vacuum/nitrogen cycles
  2. temperatureThe reaction mixture was maintained
  3. customAfter this time, the catalyst was removed by means of celite filtration
  4. concentrationthe resulting solution was concentrated under reduced pressure
  5. customCompound (IIa) was obtained quantitatively in the form of a yellow solid

Sources & evidence

ORD record
ord-c0221a464fa74fd19ae939ecffb956e6
Source dataset
uspto-grants-2014_07
Patent number
US08791294B2

Reaction notes

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