Triacetoxyperiodinane → HCID 59512332, compound

HRID 1158439Notes

Reaction equation

HRID 1158439 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:24]([CH3:26])[CH3:25])[C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[C@H:10]([CH2:27][OH:28])[CH2:9]1)=[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][C@@H:11]([CH2:13][N:14]([CH:24]([CH3:25])[CH3:26])[C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[C@H:10]([CH:27]=[O:28])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59512551HCID 59512551, compound

Product 1

HCID 59512332HCID 59512332, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a well stirred mixture of (3S,4S)-3-hydroxymethyl-4-{[isopropyl-(2-trimethylsilanyl-ethoxycarbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (16.6 g, 39.8 mmol) and Dess-Martin periodinane (16.9 g, 39.8 mmol) in CH2Cl2 (110 mL), slowly wet CH2Cl2 (0.79 mL of water in 110 mL of CH2Cl2) is added. The clear solution becomes cloudy toward the end of wet CH2Cl2 addition and is further stirred overnight. Then concentrated to a few mL of solvent by rotary evaporation and taken up in Et2O. A solution of 1:1 10% Na2S2O3 saturated aqueous NaHCO3 is added. The layers are separated and the organic extract is washed successively with H2O and brine. The aqueous washings are back-extracted with Et2O, and this organic layer is washed with H2O and brine. The combined organic layers are dried with Na2SO4, filtered and concentrated. The crude mixture is used in the next step without further purification. TLC, Rf (CH2Cl2/MeOH 9:1)=0.48. MS (LC-MS): 437.0 [M+Na]+.

Workup

  1. additionis added
  2. concentrationThen concentrated to a few mL of solvent by rotary evaporation
  3. additionA solution of 1:1 10% Na2S2O3 saturated aqueous NaHCO3 is added
  4. customThe layers are separated
  5. extractionthe organic extract
  6. washis washed successively with H2O and brine
  7. extractionThe aqueous washings are back-extracted with Et2O
  8. washthis organic layer is washed with H2O and brine
  9. dry with materialThe combined organic layers are dried with Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude mixture is used in the next step without further purification

Sources & evidence

ORD record
ord-689c4e0fceaa4337894249ad791bc42c
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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