Triethylamine → (S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 744954Notes

Reaction equation

HRID 744954 reaction equation
[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C>CS(C)=O>[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 11096562Cbz-L-Prolinol

Product 1

HCID 11746545(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred solution of N-Cbz-L-prolinol (5 g; 21.26 mmol, from steps 24b or 24c above) in 20 mL of anhydrous DMSO were added 8.89 mL (63.79 mmol) of triethylamine and 10.75 g (63.79 mmol) of SO3 -pyridine complex in 35 mL of DMSO. The reaction mixture was stirred at room temperature for 10 min; then poured into 200 mL of ice water. The mixture was extracted with ether, the extract was dried over Na2SO4 and concentrated to afford the title product, 3.058 g (70% yield).

Workup

  1. extractionThe mixture was extracted with ether
  2. dry with materialthe extract was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-58eabc93233244e7a53945419de0a047
Source dataset
uspto-grants-1996_09
Patent number
US05559242

Reaction notes

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