Potassium bisulfate → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

HRID 1821569Notes

Reaction equation

HRID 1821569 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11][CH2:10][CH2:9][C@H:2]1[C:3](N(OC)C)=[O:4].OS([O-])(=O)=O.[K+].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:12]([N:1]1[CH2:11][CH2:10][CH2:9][C@H:2]1[CH:3]=[O:4])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 6882981,1-Dimethylethyl (2S)-2-[(methoxymethylamino)carbonyl]-1-pyrrolidinecarboxylate2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

10 mmol of 30 was dissolved in 20 ml of absolute ether at 0° C. 12.5 mmol lithiumalanate was added. After 7 min of stirring 10 ml of a saturated KHSO4 solution was added drop wise. Then the mixture was diluted by adding 50 ml of ether and the organic layer was separated. This was washed by 1N HCl, water, saturated NaHCO3 solution, brine and dried. 30 (1.43 g, 5.54 mmol), LiAlH4 (0.26 g, 6.92 mmol)

Workup

  1. addition12.5 mmol lithiumalanate was added
  2. additionwas added drop wise
  3. additionThen the mixture was diluted
  4. customthe organic layer was separated
  5. washThis was washed by 1N HCl, water, saturated NaHCO3 solution, brine
  6. customdried

Sources & evidence

ORD record
ord-d46fc796f64a4c6e82b53faf94022bc9
Source dataset
uspto-grants-2009_10
Patent number
US07608577B2

Reaction notes

Loading…