Diisobutylaluminum hydride → HCID 59232219, compound

HRID 1099298Notes

Reaction equation

HRID 1099298 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=4[F:35])=[O:23])=[C:17]([F:36])[CH:16]=3)[CH:9]=[C:10]([C:11](=[O:14])[CH2:12][OH:13])[N:6]2[N:5]=[CH:4][N:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:27][C:26]=4[F:35])=[O:23])=[C:17]([F:36])[CH:16]=3)[CH:9]=[C:10]([CH:11]([OH:14])[CH2:12][OH:13])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 59231985HCID 59231985, compound

Product 1

HCID 59232219HCID 59232219, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 234 (150 mg, 0.30 mmol) in THF (2 mL) at 0° C., was added DIBAL-H (2.96 mL, 2.96 mmol, 1.0 M in THF). The reaction was allowed to stir for 30 min while warming to rt. The mixture was quenched with MeOH (1 mL) and diluted with EtOAc (300 mL) and saturated aq sodium potassium tartrate (200 mL). This solution was stirred at 50° C. for 17 hr. The mixture was allowed to cool and the organic phase was washed with brine (50 mL), dried (Na2SO4) and concentrated to dryness. The residue was purified by preparative HPLC using a gradient elution from 10% to 70% acetonitrile to obtain 31 mg (20%) of the desired product. 1H-NMR (DMSO-d6) δ 9.51 (br s, 1H), 9.35 (br s, 1H), 8.73 (d, J=6.0 Hz, 1H), 8.35 (t, J=8.7 Hz, 1H), 7.98 (s, 1H), 7.62-7.55 (m, 1H), 7.49-7.47 (m, 1H), 7.41-7.27 (m, 2H), 6.76 (s, 1H), 5.27 (t, J=5.7 Hz, 1H), 4.59-4.58 (m, 1H), 4.11 (s, 1H), 3.39 (d, J=6.9 Hz, 2H); MS [M+H]+=509.2; LCMS RT=2.98 min.

Workup

  1. customThe mixture was quenched with MeOH (1 mL)
  2. additiondiluted with EtOAc (300 mL) and saturated aq sodium potassium tartrate (200 mL)
  3. stirringThis solution was stirred at 50° C. for 17 hr
  4. temperatureto cool
  5. washthe organic phase was washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by preparative HPLC
  9. washa gradient elution from 10% to 70% acetonitrile

Sources & evidence

ORD record
ord-1f0506e2eedc45b79b5025a132cb1543
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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