Diisobutylaluminum hydride → HCID 86760572, compound

HRID 1593013Notes

Reaction equation

HRID 1593013 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)[CH2:12][C:13](N2[C@@H](C3C=CC=CC=3)[C@@H](C)N(C)C2=O)=[O:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CC(C[AlH]CC(C)C)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>ClCCl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)[CH2:12][CH:13]=[O:14])=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 24436Sodium SulfateHCID 69448484HCID 69448484, compound

Product 1

HCID 86760572HCID 86760572, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

(4R,5S)-1-[(R)-3-(4-Methanesulfonyl-phenyl)-3-thiophen-2-yl-propionyl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one (1.05 g, 2.18 mmol) was dissolved in dichloromethane (40 mL) under argon and the solution was cooled to −78° C. DIBAL solution (7 mL, 6.53 mmol) was then added dropwise and the solution stirred at −78° C. for a further 2 h. Crushed Glauber's salt (7 g) was then added and the reaction stirred vigorously at room temperature for 1 h. This was then filtered and stirred with basic alumina (7 g) for 4 h. Filtration and concentration gave the title compound (0.25 g, 38%) as a colourless oil; NMR (CDCl3): 3.05 (s, 3H), 3.24 (m, 2H), 4.96 (t, 1H), 6.85 (m, 1H), 6.93 (m, 1H), 7.20 (m, 1H), 7.48 (d, 2H), 7.90 (d, 2H), 9.76 (s, 1H).

Workup

  1. stirringthe reaction stirred vigorously at room temperature for 1 h
  2. filtrationThis was then filtered
  3. stirringstirred with basic alumina (7 g) for 4 h
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-ea79ee557ff24aeeb03c02a712add011
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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