Pyrrolidine → 4-Oxazolidinecarboxaldehyde, 3-acetyl-2,2-dimethyl-5-[4-(methylthio)phenyl]-, (4S-cis)-

HRID 1975266Notes

Reaction equation

HRID 1975266 reaction equation
N1CCCC1.[CH3:6][S:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[O:18][C:17]([CH3:20])([CH3:19])[N:16]([C:21](=[O:23])[CH3:22])[C@H:15]2[CH:24]=[O:25])=[CH:10][CH:9]=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH3:6][S:7][C:8]1[CH:9]=[CH:10][C:11]([C@@H:14]2[O:18][C:17]([CH3:19])([CH3:20])[N:16]([C:21](=[O:23])[CH3:22])[C@@H:15]2[CH:24]=[O:25])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 110554774-Oxazolidinecarboxaldehyde, 3-acetyl-2,2-dimethyl-5-[4-(methylthio)phenyl]-, (4R-trans)-

Product 1

HCID 110554764-Oxazolidinecarboxaldehyde, 3-acetyl-2,2-dimethyl-5-[4-(methylthio)phenyl]-, (4S-cis)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Pyrrolidine (9.6 mg; 0.065 mmol) was added at 25° C. to a solution of compound 4 (see example 3) (100 mg, 0.34 mmol) in toluene (2 ml) kept under magnetic stirring and under nitrogen. At the end of the addition the mixture was kept at 25° C. under stirring for 14 hours. The reaction mixture was then poured into 10% NaHCO3 ; after separation of the phases, the aqueous phase was extracted with CH2Cl2. The combined organic phases were dried over sodium sulphate and evaporated to dryness under vacuum.

Workup

  1. additionAt the end of the addition the mixture
  2. customwas kept at 25° C.
  3. stirringunder stirring for 14 hours
  4. customafter separation of the phases
  5. extractionthe aqueous phase was extracted with CH2Cl2
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-8b1e5608ff564290bde30c92ac672b59
Source dataset
uspto-grants-1994_02
Patent number
US05284966

Reaction notes

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