Triacetoxyperiodinane → tert-Butyl-(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylate

HRID 501591Notes

Reaction equation

HRID 501591 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[CH:21]=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11012982(2R,3R)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 16732142tert-Butyl-(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylateYield 108%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (51B) (6.70 g, 20.24 mmol) in CH2Cl2 (100 mL) at 0° C. was added Dess-Martin periodinane. The ice bath was removed and the reaction was warmed to rt. After 2 h, saturated aqueous Na2S2O3 and NaHCO3 (ca. 100 mL each) were added and the reaction mixture was stirred vigorously for 0.5 h. The layers were separated, the organic layer was washed with a mixture of saturated aqueous Na2S2O3 and NaHCO3 followed by brine, dried (MgSO4), and was then filtered and concentrated to obtain the title compound (7.20 g) as a yellow oil.

Workup

  1. customThe ice bath was removed
  2. additionsaturated aqueous Na2S2O3 and NaHCO3 (ca. 100 mL each) were added
  3. customThe layers were separated
  4. washthe organic layer was washed with a mixture of saturated aqueous Na2S2O3 and NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationwas then filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-33e5257d2fd24756a27297b5b79785c8
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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