Triacetoxyperiodinane → Tert-butyl 3-acetamido-4-oxopyrrolidine-1-carboxylate

HRID 2353442Notes

Reaction equation

HRID 2353442 reaction equation
[C:1]([NH:4][CH:5]1[CH:9]([OH:10])[CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)(=[O:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[C:1]([NH:4][CH:5]1[C:9](=[O:10])[CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68711974Tert-butyl 3-acetamido-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 68716973Tert-butyl 3-acetamido-4-oxopyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-(acetylamino)-4-hydroxypyrrolidine-1-carboxylate obtained in Step A (680 mg) in dichloromethane (8 mL) was treated with 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (1.77 g) and stirred overnight at room temperature. The solution was then evaporated and purified on a Biotage Horizon® system (silica, gradient 50-90% ethyl acetate in hexane) to yield the title compound. LC-MS 243.2 (M+1).

Workup

  1. customThe solution was then evaporated
  2. custompurified on a Biotage Horizon® system (silica, gradient 50-90% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-324fac426baf4d73960bc895d40575ce
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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