Diisobutylaluminum hydride → Z-(1R,6R)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

HRID 40627Notes

Reaction equation

HRID 40627 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[C:18](=O)[CH:17]2[NH:20][C:21](=O)[CH:12]1[CH2:13][CH:14]=[CH:15][CH2:16]2.CC(C[AlH]CC(C)C)C>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:18][C@@H:17]2[NH:20][CH2:21][C@H:12]1[CH2:13][CH:14]=[CH:15][CH2:16]2

Participants

3

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 692342217-Naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione

Product 1

HCID 59686806Z-(1R,6R)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

Conditions

Temperature
130 °C

Procedure

7-Naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione (130 mg, 0.45 mmol) and DiBAl-H (6 mL, 1M, 6 mmol) were placed in a μW tube under argon vent. The reaction mixture was then heated to 130° C. for 900 sec. The reaction was quenched with Rochelle's salt and diethyl ether mixture (1:1, 200 mL) and then stirred overnight. The organic eas layer separated and dried with magnesium sulfate, filtered and solvent evaporated under reduced pressure to yield the title compound as a residue.

Workup

  1. customThe reaction was quenched with Rochelle's salt and diethyl ether mixture (1:1, 200 mL)
  2. customThe organic eas layer separated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customsolvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-635d55a2d41149b8b4a634b7521f7c58
Source dataset
uspto-grants-2013_09
Patent number
US08530475B2

Reaction notes

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