HCID 54407029, compound → HCID 73450239, compound

HRID 1267601Notes

Reaction equation

HRID 1267601 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:8]([CH2:13][O:14][S:15]([CH3:18])(=[O:17])=[O:16])([CH2:9][N:10]=[N+]=[N-])[CH2:7][N:6]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:5]1.[H][H]>C(OCC)(=O)C.[Ni]>[CH3:1][O:2][N:3]=[C:4]1[C:8]([CH2:13][O:14][S:15]([CH3:18])(=[O:16])=[O:17])([CH2:9][NH2:10])[CH2:7][N:6]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:5]1

Participants

5

Reactant 2

HCID 54407029HCID 54407029, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 73450239HCID 73450239, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-benzyl-4-methanesulfonyloxymethyl-4-azidomethyl-pyrrolidine-3-one-O-methyloxime was dissolved in 100 ml of ethyl acetate and thereto 5 ml of 50% Raney nickel slurry was added and the resulting mixture was stirred for 3 hours under the pressure of hydrogen. The reaction mixture was filtered and concentrated under the reduced pressure to give 8.0 g of 1-benzyl-4-methanesulfonyloxymethyl-4-aminomethyl-pyrrolidine-3-one-O-methyloxime (yield: 86%). The obtained compound was dissolved in 200 ml of acetonitrile and thereto 3.9 ml of 1,8-diazabicyclo[5,4,0]undec-7-ene was dropped, and the resulting mixture was stirred for 8 hours, concentrated under the reduce pressure, and dissolved in 150 ml of dichloromethane, washed with 100 ml of water and with 100 ml of saline solution, dried with magnesium sulfate, filtered and concentrated under the reduced pressure to give 4.0 g of 6-benzyl-2,6-diazaspiro[3,4]octane-8-one-O-methyloxime (yield: 69.3%). The obtained compound and 2.5 ml of triethylamine were dissolved in 50 ml of dichloromethane and thereto 3.9 g of di-t-butyldicarbonate. The resulting mixture was stirred for 4 hours, washed with 50 ml of water, dried with magnesium sulfate, filtered and concentrated under the reduced pressure. The concentrated residue was purified by silicagel column chromatography(ethylacetate:normal hexane:dichloromethane=3:5:1) to give 4.6 g of the titled compound (yield: 80.9%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under the reduced pressure

Sources & evidence

ORD record
ord-af7823c77a0f48b1964a33ae7148c8d9
Source dataset
uspto-grants-2003_04
Patent number
US06552196B2

Reaction notes

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