Diisobutylaluminum hydride → HCID 10073505, compound

HRID 1830507Notes

Reaction equation

HRID 1830507 reaction equation
CC(C[AlH]CC(C)C)C.[OH:10][C:11]1[CH:12]=[CH:13][C:14]2[C:18]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:23][CH:22]=3)=[O:20])=[C:17]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3O)[S:16][C:15]=2[CH:44]=1>C1COCC1>[N:30]1([CH2:29][CH2:28][O:27][C:24]2[CH:23]=[CH:22][C:21]([CH:19]3[C:18]4[C:14]5[CH:13]=[CH:12][C:11]([OH:10])=[CH:44][C:15]=5[S:16][C:17]=4[CH2:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][C:42]=4[O:20]3)=[CH:26][CH:25]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 10345357HCID 10345357, compound

Product 1

HCID 10073505HCID 10073505, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add DIBAL solution (5 mL, 1M/THF) dropwise to [6-hydroxy-2-(2-hydroxy-benzyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (300 mg, 0.6 mmol) in THF (5 mL) at −78° C. Stir for 30 min and quench with water, followed by TFA (5 mL). Stir the mixture for 3 h while warming to r.t. Remove the solvent in vacuo and dissolve the residue in i-PrOH/CH2Cl2 (1:3). Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate. Purify by flash chromatography (0–5% (2M NH3 in MeOH)/CH2Cl2) to afford 5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-6-oxa-12-thia-dibenzo[a,f]azulen-2-ol (180 mg, 62%).

Workup

  1. customquench with water
  2. stirringStir the mixture for 3 h
  3. customRemove the solvent in vacuo
  4. dissolutiondissolve the residue in i-PrOH/CH2Cl2 (1:3)
  5. washWash the organic phase with water and brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify by flash chromatography (0–5% (2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-396b101dcb8e4e1db75fb96ce30d1144
Source dataset
uspto-grants-2006_06
Patent number
US07067510B2

Reaction notes

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