D-Psicose → (4-Amino-3-methoxyphenyl)(aziridin-1-yl)methanone

HRID 1487622Notes

Reaction equation

HRID 1487622 reaction equation
[N:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([O:15][CH3:16])[CH:7]=2)=[O:5])[CH2:3][CH2:2]1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CO.[Pd]>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]([N:1]2[CH2:3][CH2:2]2)=[O:5])=[CH:7][C:8]=1[O:15][CH3:16]

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 86726450Aziridin-1-yl(3-methoxy-4-nitrophenyl)methanone

Product 1

HCID 86726451(4-Amino-3-methoxyphenyl)(aziridin-1-yl)methanoneYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of aziridin-1-yl(3-methoxy-4-nitrophenyl)methanone (1 equiv) in MeOH (0.24 M) was added 10% palladium on carbon (25% by weight). The reaction mixture was stirred at 50° C. under hydrogen atmosphere (50 Psi) overnight then filtered through celite. The filtrate was concentrated and the residue was purified by silica gel chromatography (50% ethyl acetate in petroleum ether) to afford the title compound (33% yield) as a yellow solid. MS (ESI) m/z 193.1 [M+1]+.

Workup

  1. filtrationthen filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel chromatography (50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-0a28f0eb603d4f218ec43f6a118927e3
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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