Diisobutylaluminum hydride → HCID 19384500, compound

HRID 2399787Notes

Reaction equation

HRID 2399787 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:13]3[CH:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:15][CH2:16][CH2:17][C:12]=3[NH:11][C:10]=2[CH:26]=1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[CH2:18]([CH:14]1[C:13]2[C:9]3[CH:8]=[CH:7][C:6]([CH2:4][OH:3])=[CH:26][C:10]=3[NH:11][C:12]=2[CH2:17][CH2:16][CH2:15]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 19384586HCID 19384586, compound

Product 1

HCID 19384500HCID 19384500, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 30.4 g of 5,6,7,8-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrole-3-carboxylic acid ethyl ester from Example 9, in 300 ml of methylene chloride was treated with 124 ml of a 1.5M DIBAH solution in toluene at 0°-5° C. (ice-water bath) in approximately 20 minutes. After an additional 20 minutes stirring at the same temperature, the reaction mixture was cautiously poured into cold 2N-HCl ice and extracted with methylene chloride. The organic extracts were washed with water and brine, then dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 28.3 g of a crude yellow oil. Purification of this material on a small silica gel pad (eluting system:hexane-ethyl acetate 1:1) produced 25.8 g (96.2%) of 5,6,7,8-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrole-3-methanol as a yellow oil.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic extracts were washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give 28.3 g of a crude yellow oil
  7. customPurification of this material
  8. washon a small silica gel pad (eluting system:hexane-ethyl acetate 1:1)

Sources & evidence

ORD record
ord-1414b27ed05347dbb9bc7feff71de9cf
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

Loading…