Methanol → HCID 22872486, compound

HRID 1779501Notes

Reaction equation

HRID 1779501 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C@@H:4]1[C@@H:8]([CH2:9][CH3:10])[CH2:7][CH2:6][NH:5]1.[OH-:12].[Na+].[CH3:14][OH:15]>>[CH3:1][O:2][C:3](=[O:11])[C@@H:4]1[C@H:8]([CH2:9][CH3:10])[CH2:7][CH2:6][N:5]1[C:14]([O:15][C:8]([CH3:9])([CH3:4])[CH3:7])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11116310HCID 11116310, compound

Product 1

HCID 22872486HCID 22872486, compound

Conditions

Temperature
0 °C

Procedure

N-[(tert Butyloxy)carbonyl]-cis, trans-3-ethylproline methyl ester (29.1 g, 0.113 mol) was dissolved in CH3OH (114 mL) with cooling to 0° C., then treated with 1N NaOH (114 mL). After stirring for 20 h at 23° C., the solution was concentrated to remove the CH3OH and then extracted with EtOAc (3×). The organic layers were combined, dried (MgSO4), filtered, and concentrated to give 12.8 g of N-[(tert-Butyloxy)carbonyl]-cis-3-ethylproline methyl ester as an oil. The aqueous layer was acidified with solid citric acid and extracted with EtOAc (2×), the organic layers combined, dried (MgSO4), filtered, and concentrated to give N-[(tert Butyloxy)carbonyl]-trans 3-ethylproline as an oil. 1H NMR (CD3OD) δ3.86 and 3.78 (2 d, 1H, J=6 Hz), 3.33-3.58 (m, 2H), 2.01-2.22 (m, 2H), 1.5-1.74 (m, 2H), 1.33-1.5 (m, 1H), 1.45 and 1.42 (2 s, 9H), 0.98 (t, 3H, J=8 Hz).

Workup

  1. concentrationthe solution was concentrated
  2. customto remove the CH3OH
  3. extractionextracted with EtOAc (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-696c6ce4d19342c7ae74c94d35b4a382
Source dataset
uspto-grants-1997_05
Patent number
US05627202

Reaction notes

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