Formaldehyde → 4-Methoxycarbonyl-3-methyl-2-phenylthiazolidine

HRID 2081506Notes

Reaction equation

HRID 2081506 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][S:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:6]1)=[O:4].C=O.[C:18]([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C(O)(=O)C.C(#N)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][S:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]1[CH3:18])=[O:4]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 147909142-Phenylthiazolidine-4-carboxylic acid methyl ester

Product 1

HCID 150522574-Methoxycarbonyl-3-methyl-2-phenylthiazolidineYield 100%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2.23 g of 4-methoxycarbonyl-2-phenylthiazolidine in 20 m of acetonitrile was chilled to -15° C. and, after addition of 4.3 g of 35% formalin and 1.0 g of sodium cyanoborohydride, was stirred for 30 minutes. The mixture was made acidic by addition of acetic acid under chilling with ice and, after addition of water, was made alkaline by addition of potassium carbonate. The alkaline solution was extracted with ether, and the etheral extract was dried over anhydrous sodium sulfate. The extract was placed under reduced pressure to distill of the solvent. The residue was purified by silica gel column chromatography (eluent: chloroform) to give 2.37 g of 4-methoxycarbonyl-3-methyl-2-phenylthiazolidine as a colorless oil.

Workup

  1. temperatureunder chilling with ice
  2. extractionThe alkaline solution was extracted with ether
  3. extractionthe etheral extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. distillationto distill of the solvent
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-d0fde7f5f32b4592968dcf896533d930
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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