Triacetoxyperiodinane → (1-Formylcyclopropyl)carbamic acid tert-butyl ester

HRID 1187652Notes

Reaction equation

HRID 1187652 reaction equation
[OH:1][CH2:2][C:3]1([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([C:3]1([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[CH3:12])[CH2:5][CH2:4]1)=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11286907tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate

Product 1

HCID 10352385(1-Formylcyclopropyl)carbamic acid tert-butyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (Bioorg. Med. Chem. Lett., 2008, 18(6), 2188) (135 mg, 0.72 mmoles) in DCM (8 mL) was added Dess-Martin periodinane (277 mg, 0.65 mmole). After stirring 1 hr, the reaction was filtered through celite and concentrated to a yellow oil which was further purified by Isolera (7%-70% ethyl acetate/hexanes) to provide 84 mg (87%) of tert-butyl (l-formylcyclopropyl)-carbamate as a white solid.

Workup

  1. filtrationthe reaction was filtered through celite
  2. concentrationconcentrated to a yellow oil which
  3. customwas further purified by Isolera (7%-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-318090acc0e94929bba6d033cc419b86
Source dataset
uspto-grants-2014_03
Patent number
US08673925B1

Reaction notes

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