HCID 68489074, compound → HCID 68488928, compound

HRID 723866Notes

Reaction equation

HRID 723866 reaction equation
C1(C[O:8][CH2:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([N:21]4[CH2:25][C@H:24]([C:26]([O:28][CH3:29])=[O:27])[O:23][C:22]4=[O:30])=[CH:18][CH:19]=3)[CH2:14][C@H:13]2[CH3:31])=[O:11])C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].CO>[OH:8][CH2:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([N:21]3[CH2:25][C@H:24]([C:26]([O:28][CH3:29])=[O:27])[O:23][C:22]3=[O:30])=[CH:18][CH:19]=2)[CH2:14][C@H:13]1[CH3:31])=[O:11]

Participants

5

Reactant 2

HCID 68489074HCID 68489074, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68488928HCID 68488928, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of methyl (5R)-3-[(2R)-2,3-dihydro-1-[(phenylmethoxy)acetyl]-2-methyl-1H-indol-5-yl]-2-oxo-5-oxazolidinecarboxylate (Step 1, 0.301 g, 0.71 mmol) and Pearlman's catalyst (0.032 g) in methanol (30 mL) is shaken on a Parr apparatus under a 36 psi hydrogen atmosphere for approximately 24 h, during which additional Pearlman's catalyst (0.044 g) is added. The catalyst is removed by filtration through a pad of Celite, and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on a Biotage Flash 40S silica gel cartridge (2% MeOH/CH2Cl2 eluent) to give the title compound, MS (ESI+) for C16H18N2O6 m/z 335 (M+H)+.

Workup

  1. additionis added
  2. customThe catalyst is removed by filtration through a pad of Celite
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is purified by chromatography on a Biotage Flash 40S silica gel cartridge (2% MeOH/CH2Cl2 eluent)

Sources & evidence

ORD record
ord-0cd10b16386c4cf88a387e0ac5c0d32d
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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