HCID 86726490, compound → HCID 86726489, compound

HRID 1487657Notes

Reaction equation

HRID 1487657 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:5][N@:4]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([O:17][CH3:18])[CH:9]=1)=[O:7]>CO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([N@@:4]2[CH2:5][CH:3]2[CH2:2][OH:1])=[O:7])=[CH:9][C:10]=1[O:17][CH3:18]

Participants

4

Reactant 1

HCID 86726490HCID 86726490, compound

Product 1

HCID 86726489HCID 86726489, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-(2-(hydroxymethyl)aziridin-1-yl)(3-methoxy-4-nitrophenyl)methanone (1 equiv) in MeOH (0.12 M) was added 10% palladium on charcoal (67 weight %). The reaction mixture was stirred at 50° C. under hydrogen atmosphere (50 psi) overnight and then filtered through celite. The filtrate was concentrated and the residue was purified by silica gel chromatography (0-10% DCM in MeOH) to afford the desired product (92% yield) as a white solid. MS (ESI) m/z 223.2 [M+H]+.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel chromatography (0-10% DCM in MeOH)

Sources & evidence

ORD record
ord-e21cd9f0631042638a99baac06d6915a
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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