Ammonium formate → (4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-ethanone

HRID 566798Notes

Reaction equation

HRID 566798 reaction equation
C(O[CH:5]([C:22]1[CH:26]=[CH:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[CH:23]=1)[C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])(=O)C.C([O-])=O.[NH4+].CCOC(C)=O.C(Cl)Cl>[Pd].CCOC(C)=O.CCO>[CH2:13]([C@H:12]1[CH2:11][O:10][C:9]([CH3:21])([CH3:20])[N:8]1[C:6](=[O:7])[CH2:5][C:22]1[CH:26]=[CH:25][N:24]([C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[CH:31][CH:32]=2)[CH:23]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 2723923Ammonium formateHCID 183412742-acetoxy-1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-ethanoneHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 18341259(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-ethanoneYield 43%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of crude 2-acetoxy-1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-[1-(biphenyl-4-yl)-1H-pyrrol-3-yl]-ethanone (1.82 mmol) and 10% palladium on carbon (120 mg) in EtOAc (4.5 mL) and EtOH (4.5 mL) was added ammonium formate (0.58 g, 9.2 mmol). After 40 hours at ambient temperature, the resultant mixture was filtered and the filtrate concentrated to a residue which was dissolved in EtOAc, washed with 1M pH7 phosphate buffer, dried over Na2SO4, and evaporated under reduced pressure to give a crude product. Flash column chromatography with 0-4% EtOAc/CH2Cl2 gradient eluant yielded 220 mg (43%) of 1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-[1-(biphenyl-4-yl)-1H-pyrrol-3-yl]-ethanone as a pale yellow amorphous solid. 1H NMR: δ 7.62 (t, 4H, J=9.4 Hz), 7.47 (d, 2H, J=7.4 Hz), 7.42 (d, 2H, J=8.5 Hz), 7.35 (t, 2H, J=6.6 Hz), 7.30-7.21 (m, 4H), 7.08 (t, 1H, J=2.6 Hz), 7.05 (s, 1H), 6.28 (t, 1H, J=2.21 Hz), 4.16-4.10 (m, 1H), 3.82 (m, 2H), 3.62, 3.54 (AB quartet, 2H, J=15.5 Hz), 3.07 (dd, 1H, J=3.9, 13.8 Hz), 2.91 (dd, 1H, J=9.9, 13.6 Hz), 1.78 (s, 3H), 1.59 (s, 3H). Anal. Calculated for C30H30N2O2•0.25 H2O: C, 79.18; H, 6.76; N, 6.16. Found: C, 79.24; H, 6.79; N, 6.12.

Workup

  1. filtrationthe resultant mixture was filtered
  2. concentrationthe filtrate concentrated to a residue which
  3. dissolutionwas dissolved in EtOAc
  4. washwashed with 1M pH7 phosphate buffer
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customto give a crude product

Sources & evidence

ORD record
ord-892bae611b0d40d78f3eaa0e970c4e7b
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

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