Cornforth reagent → 1810076-94-8

HRID 1477946Notes

Reaction equation

HRID 1477946 reaction equation
[OH:1][CH:2]1[C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[O:1]=[C:2]1[C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 118390034HCID 118390034, compound

Product 1

HCID 1183900101810076-94-8Yield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-2-azaspiro[4.4]nonane-2-carboxylate (10.82 g, 44.8 mmol) in DCM (225 mL) was added 4 Å molecular sieve (22.00 g), then added PDC (42.17 g, 112.1 mmol) slowly. After addition, the reaction mixture was stirred at rt overnight and filtered. The filter cake was washed with EtOAc (50 mL×3) and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/15) to give the product as colorless oil (5.92 g, 55.2%).

Workup

  1. additionAfter addition
  2. filtrationfiltered
  3. washThe filter cake was washed with EtOAc (50 mL×3)
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/15)

Sources & evidence

ORD record
ord-141752707e32451f880ca53ab5638a9d
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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