Methanol → HCID 22881695, compound

HRID 727550Notes

Reaction equation

HRID 727550 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@:10]([CH2:21][CH:22]([CH3:24])[CH3:23])([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:9]1=[O:25])=O)(C)(C)C.C[O-].[Mg+2].C[O-].CO.O>C(O)(=O)C>[CH3:23][CH:22]([CH3:24])[CH2:21][C@@:10]1([CH2:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:11][CH2:12][NH:8][C:9]1=[O:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 164537Methanol, magnesium salt (2:1)HCID 53993408HCID 53993408, compound

Product 1

HCID 22881695HCID 22881695, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (S)-tert-butyl N-tert-butyloxycarbonyl-3-(2-methylpropyl)-2-oxo-3-pyrrolidineacetate (193 mg, 0.543 mmol), magnesium methoxide (3.0 mL, 6-10 wt. % in MeOH), and MeOH (2.7 mL) is stirred at room temperature for 16 hours. The solution is poured into water (15 mL) and the mixture acidified with acetic acid. The mixture is extracted several times with CH2Cl2, the combined filtrates dried (MgSO4), filtered, and concentrated to give 124 mg (89%) of the title compound as an oil.

Workup

  1. extractionThe mixture is extracted several times with CH2Cl2
  2. dry with materialthe combined filtrates dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5e1725f2c11841cfbe34de2a79a482d8
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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