n-Tert-butoxycarbonyl-(r)-(-)thiazolidine-4-carboxylic acid-n-methoxy-n-methyl amide → N-tert-butoxycarbonyl-(R)-(-)thiazolidine-4-carboxaldehyde

HRID 383115Notes

Reaction equation

HRID 383115 reaction equation
CON(C)[C:4]([C@@H:6]1[CH2:10][S:9][CH2:8][N:7]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:14]([O:13][C:11]([N:7]1[C@H:6]([CH:4]=[O:5])[CH2:10][S:9][CH2:8]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 20699041n-Tert-butoxycarbonyl-(r)-(-)thiazolidine-4-carboxylic acid-n-methoxy-n-methyl amideHCID 21226445Aluminium lithium hydride

Product 1

HCID 20699040N-tert-butoxycarbonyl-(R)-(-)thiazolidine-4-carboxaldehydeYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. solution in THF (6 mL) of N-tert-butoxycarbonyl-(R)-(−)thiazolidine-4-carboxylic acid-N-methoxy-N-methyl amide (550 mg, 2.0 mmol) was added lithium aluminum hydride (1.0 M in THF, 3.0 mL, 3.0 mmol) and the reaction mixture was stirred for 2.5 hours. The reaction was quenched with 10% aqueous citric acid (30 mL) and warmed to ambient temperature. The mixture was warmed to ambient temperature and extracted with ether (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give N-tert-butoxycarbonyl-(R)-(−)thiazolidine-4-carboxaldehyde (440 mg) which was used without further purification.

Workup

  1. customThe reaction was quenched with 10% aqueous citric acid (30 mL)
  2. temperatureThe mixture was warmed to ambient temperature
  3. extractionextracted with ether (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f63b6b35104e4aee9c7a0f733fb45570
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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