Potassium Sodium Tartrate → HCID 68535289, compound

HRID 2389345Notes

Reaction equation

HRID 2389345 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][N:14]3[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[O:8][CH:9]=1)=O.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl.C(Cl)(Cl)Cl>[OH:2][CH2:3][C:5]1[N:6]=[C:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][N:14]3[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[O:8][CH:9]=1

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydride2×HCID 68537460HCID 68537460, compound

Product 1

HCID 68535289HCID 68535289, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of tert-butyl 4-[4-(methoxycarbonyl)-1,3-oxazol-2-yl]-1H-indole-1-carboxylate (512 mg) in DCM (10.2 mL) was added dropwise 1M DIBAL in DCM solution (4.2 mL) at 0° C. and the mixture was stirred at the same temperature for 1.5 hours. 1M DIBAL in DCM solution (0.60 mL) was added dropwise to the mixture. The mixture was stirred at 0° C. for 1.5 hours. To the resulting solution was added dropwise 1M Rochelle salt aqueous solution (25.0 mL) and the suspension was stirred at ambient temperature for overnight. The suspension was diluted with chloroform (50.0 mL) and filtered through a bed of celite. The layers were separated and the organic layer was washed with 0.5 M Rochelle salt solution, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=2:1) to give tert-butyl 4-[4-(hydroxymethyl)-1,3-oxazol-2-yl]-1H-indole-1-carboxylate.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1.5 hours
  2. stirringthe suspension was stirred at ambient temperature for overnight
  3. filtrationfiltered through a bed of celite
  4. customThe layers were separated
  5. washthe organic layer was washed with 0.5 M Rochelle salt solution
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=2:1)

Sources & evidence

ORD record
ord-0a837084a72049678bae129d947c25d6
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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