Triacetoxyperiodinane → tert-butyl 3-methyl-4-oxopyrrolidine-1-carboxylate

HRID 252094Notes

Reaction equation

HRID 252094 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)O[C:12](=O)[C:11]2[CH:10]=C[CH:8]=[CH:7][C:6]1=2)=O.[C:23]([O:27][C:28]([N:30]1[CH2:34][C@@H:33]([CH3:35])[C@H:32]([OH:36])[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>ClCCl>[CH3:10][CH:11]([CH2:6][CH2:7][CH3:8])[CH3:12].[C:23]([O:27][C:28]([N:30]1[CH2:31][C:32](=[O:36])[CH:33]([CH3:35])[CH2:34]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 53302312tert-butyl (3S,4R)-3-hydroxy-4-Methylpyrrolidine-1-carboxylate

Product 2

HCID 78922-MethylpentaneHCID 57741675tert-butyl 3-methyl-4-oxopyrrolidine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cool down a suspension of Dess Martin periodinane (1.1 g, 2.6 mmol) in dry dichloromethane (5 mL) under nitrogen with an ice bath and add a solution of trans-3-hydroxy-4-methylpyrrolidine-1-carboxylic acid tert-butyl ester (350 mg, 1.73 mmol) in dry dichloromethane (2 mL). Stir under nitrogen and allow to warm up to room temperature overnight. Add saturated aqueous sodium hydrogen carbonate, then saturated aqueous sodium thiosulfate and extract with dichloromethane. Combine the organic layers and wash with saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and chromatograph on silica gel, eluting with 0:100 to 40:60 ethyl acetate:2-methylpentane to give 3-methyl-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester (240 mg, 70%). 1H NMR (300 MHz, CDCl3) δ 4.06-4.19 (1H, m), 3.84-3.98 (1H, m), 3.61-3.72 (1H, m), 3.17 (1H, dd, J=11.11, 9.04 Hz), 2.56-2.70 (1H, m, J=7.72 Hz), 1.49 (9H, s), 1.18 (3H, d, J=7.16 Hz), MS (ES): m/z=222 [M+Na].

Workup

  1. extractionAdd saturated aqueous sodium hydrogen carbonate, then saturated aqueous sodium thiosulfate and extract with dichloromethane
  2. washwash with saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. washchromatograph on silica gel, eluting with 0:100 to 40:60 ethyl acetate

Sources & evidence

ORD record
ord-dd8b0e6d81cf447da6044769cd394a23
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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