Ammonium formate → HCID 66705807, compound

HRID 1187760Notes

Reaction equation

HRID 1187760 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66705805HCID 66705805, compound

Product 1

HCID 66705807HCID 66705807, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of (S)-2,2-dimethyl-4-[(E)-2-(4-nitro-phenyl)-vinyl]-oxazolidine-3-carboxylic acid tert-butyl ester (12.0 g) in methanol (500 ml) were added ammonium formate (32.6 g) and palladium on charcoal (1.83 g, 10 wt %) and the mixture was heated at 50° C. for 1 hour. The mixture was then cooled to room temperature, filtered through celite and the filtrate was concentrated in vacuo. The residue was then taken up in ethyl acetate and washed with water. The phases were separated and the organic phase was dried over sodium sulphate and concentrated in vacuo. The reside was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (8.72 g, 79%) as a yellow oil. MS (ISP): 321.4 ([M+H]+).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. washwashed with water
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe reside was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

Sources & evidence

ORD record
ord-c82d77f4eb0d4a08a617384cc552c266
Source dataset
uspto-grants-2014_03
Patent number
US08673950B2

Reaction notes

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