1-Boc-3-pyrrolidinol → Tert-butyl 3-oxopyrrolidine-1-carboxylate

HRID 275815Notes

Reaction equation

HRID 275815 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(Cl)Cl.C(OCC)C>[C:1]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateYield 73.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-Boc-3-pyrrolodinol (17.192 g, 0.092 mole) in 50 mL anhydrous methylene chloride was added to a solution of (60 g, 0.276 mole) of pyridinechlorochromate in 300 mL anhydrous methylene chloride which was surrounded by a water bath at room temperature. After stirring at room temperature for 4 hours an additional (60 g, 0.276 mole) of pyridinechlorochromate was added and the reaction was stirred over night. The reaction had gone to completion by the next morning and was diluted with 400 mL diethyl ether and filtered through a pad of celite 521 filter aid using excess diethyl ether to wash through. Evaporation gave a black oil which was flash chromatographed over silica gel eluting with 40% ethyl acetate in hexane to provide the title compound (12.5 g, 71%) as an oil. Mass Spec FD+MI=184.9, (MW=185) 1H NMR (300 MHz CDCl3) δ 1.49 (9H, s); 2.56-2.61 (2H, t); 3.75-3.80 (4H, t).

Workup

  1. customwas surrounded by a water bath at room temperature
  2. additionwas added
  3. stirringthe reaction was stirred over night
  4. filtrationfiltered through a pad of celite 521
  5. filtrationfilter aid
  6. washto wash through
  7. customEvaporation
  8. customgave a black oil which
  9. customchromatographed over silica gel eluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1b3fa26afbab46188e2addef2c38acdb
Source dataset
uspto-grants-2002_03
Patent number
US06353008B1

Reaction notes

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