Diisobutylaluminum hydride → HCID 178435560, compound

HRID 348523Notes

Reaction equation

HRID 348523 reaction equation
C([C:3]1[CH:11]=[CH:10][C:9]2[N:8](CC)[C:7]3[CH2:14][CH2:15][CH2:16][C:6]=3[C:5]=2[CH:4]=1)#N.CC(C[AlH]C[CH:23]([CH3:25])C)C.[C:26](C(C(C([O-])=O)O)O)([O-])=[O:27].[K+].[Na+]>ClCCl>[CH2:23]([C:16]1[C:6]2[C:7]([N:8]=[C:9]3[C:5]=2[CH:4]=[CH:3][CH:11]=[C:10]3[CH:26]=[O:27])=[CH:14][CH:15]=1)[CH3:25]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 21087561HCID 21087561, compound

Product 1

HCID 178435560HCID 178435560, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-cyano-4-ethyl-1,2,3,4-tetrahydrocyclopent[b]indole (0.28 g, 1.33 mmol) in dichloromethane (15 mL) was cooled in an ice-bath then treated with DIBAL-H (0.189 g, 1.33 mmol). The reaction was then allowed to reach room temperature and was stirred for 15 hours before diluting with dichloromethane and pouring into a saturated solution of sodium potassium tartrate. The organic layer was separated then washed with brine. The crude product was purified by column chromatography eluting with dichloromethane, to afford 0.2 g of title compound.

Workup

  1. customto reach room temperature
  2. customThe organic layer was separated
  3. washthen washed with brine
  4. customThe crude product was purified by column chromatography
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-94079b0506ec40cfac4d8c432075f48e
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

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