Diisobutylaluminum hydride → HCID 57680885, compound

HRID 422655Notes

Reaction equation

HRID 422655 reaction equation
CC(C[AlH]CC(C)C)C.CON(C)[C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][C:19]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[N:18]2)=[O:14].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[C:25]1([C:19]2[CH:20]=[N:21][C:22]3[C:17]([N:18]=2)=[CH:16][C:15]([CH:13]=[O:14])=[CH:24][CH:23]=3)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 57680935HCID 57680935, compound

Product 1

HCID 57680885HCID 57680885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

DIBAL (1.0 M in THF, 2.0 mL, 2.0 mmol was added to a THF (5 mL) solution of N-methoxy-N-methyl-3-phenylquinoxaline-6-carboxamide (198 mg, 0.67 mmol) under N2 over 10 min at −78° C. The reaction was stirred for 2.5 h at the temperature, then satd solution of potassium sodium tartrate (Rochelle salt), was added. The cooling bath was removed immediately after the addition. The reaction was stirred for 30 min turning into a clear orange solution. The crude mixture was extracted with DCM (3×), washed (satd Rochelle salt, brine), dried, concentrated and purified by flash chromatography (SiO2, 0-1.5% MeOH in DCM) to afford the title compound as a white solid; 1H NMR (400 MHz, CDCl3) δ 10.27 (s, 1H), 9.43 (s, 1H), 8.63 (s, 1H), 8.26-8.20 (m, 4H), 7.65-7.52 (m, 3H), MS (ES+): m/z 235.1 (100) [MH+]; HPLC: tR=3.38 min (OpenLynx, polar—5 min).

Workup

  1. additionwas added
  2. customThe cooling bath was removed immediately
  3. additionafter the addition
  4. stirringThe reaction was stirred for 30 min
  5. extractionThe crude mixture was extracted with DCM (3×)
  6. washwashed (satd Rochelle salt, brine)
  7. customdried
  8. concentrationconcentrated
  9. custompurified by flash chromatography (SiO2, 0-1.5% MeOH in DCM)

Sources & evidence

ORD record
ord-70cfde07e885499d9fbfbf91835c8d90
Source dataset
uspto-grants-2012_01
Patent number
US08101613B2

Reaction notes

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