Ethyl Acetate → HCID 59614349, compound

HRID 409472Notes

Reaction equation

HRID 409472 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C@H:10]([OH:15])[C@@H:9]1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>ClCCl.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C:10](=[O:15])[C@@H:9]1[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 59614360HCID 59614360, compound

Product 1

HCID 59614349HCID 59614349, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (2S,3S,5R)-2-benzyl-5-ethyl-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.138 mmol; 42 mg) in dichloromethane (1.4 mL) is added Dess-Martin periodinane (0.166 mmol; 70.4 mg) at 0° C. The mixture is stirred at the same temperature for 1.5 hours. To the mixture, brine and EtOAc are added. The organic layer is separated, washed with saturated aqueous Na2S2O3 solution, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give (2S,5R)-2-benzyl-5-ethyl-3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (29.8 mg, 71%); ESI-MS m/z: 248 [M+−tBu+2], Retention time 2.49 min (condition A).

Workup

  1. customThe organic layer is separated
  2. washwashed with saturated aqueous Na2S2O3 solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc)

Sources & evidence

ORD record
ord-0a595b992eaa40938c532185683ca771
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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