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

HRID 21768

Reaction equation

HRID 21768 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-dde2fa59cbf74121a07de79c5cab1323
Source dataset
uspto-grants-1995_06
Patent number
US05424444

Linked notes

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