Acetic Acid → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

HRID 653844Notes

Reaction equation

HRID 653844 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH2:13][C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(O)(=O)C>C(Cl)Cl>[CH:13]([C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 643448(S)-(-)-N-Boc-prolinolHCID 178418287HCID 178418287, compound

Product 1

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Example 2, 16.0 g of pyridinium chlorochromate, 10.0 g of (S)-2-(hydroxymethyl)-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester, 36.0 g of crushed 4 Å molecular sieves and 4.5 ml of glacial acetic acid in 250 ml of methylene chloride gives 6.8 g of the product as a yellow oil.

Sources & evidence

ORD record
ord-d48d8c8823034429aa71ce44836a5f88
Source dataset
uspto-grants-1992_07
Patent number
US05128483

Reaction notes

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