Diisobutylaluminum hydride → HCID 86644086, compound

HRID 1776683Notes

Reaction equation

HRID 1776683 reaction equation
[C:1]([O:9][C:10]1[C:27]([O:28][CH3:29])=[CH:26][C:13]([C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]2[C:22](OC)=[O:23])=[O:15])=[C:12]([N+:30]([O-:32])=[O:31])[CH:11]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl.C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:1]([O:9][C:10]1[C:27]([O:28][CH3:29])=[CH:26][C:13]([C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]2[CH:22]=[O:23])=[O:15])=[C:12]([N+:30]([O-:32])=[O:31])[CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 59440207HCID 59440207, compound

Product 1

HCID 86644086HCID 86644086, compoundYield 109%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 23443464Methane, dichloro-, compd. with benzene (1:1)Solvent

Conditions

Temperature
-78 °C

Procedure

(R)-Methyl 1-(4-(benzoyloxy)-5-methoxy-2-nitrobenzoyl)piperidine-2-carboxylate (1.50 g, 3.50 mmol) in 30 ml of 1:1 DCM/benzene at −78° C. was added 7.5 ml of 1.0 M DIBAL in toluene under Ar in 10 min. The mixture was stirred at −78° C. for 1 hr and the reaction was quenched with 0.5 ml of methanol. The mixture was diluted with 150 ml of EtAc and 100 ml of 0.2 M HCl. The organic solvent layer was separated and was separated and the aqueous layer was extracted with EtOAc (3×80 ml). The organics were combined, dried over MgSO4, filtered, concentrated and purified on SiO2 chromatography eluted with EtAc/hexane (3:2) to afford 1.52 g (90%) of the title product. 1H NMR (CDCl3), 9.60 (s, 1H), 7.70 (s, 1H), 7.65-7.28 (m, 5H), 6.78 (m, 1H), 5.16 (s, 2H), 3.92 (s, 3H), 3.22, (m, 1H), 3.01 (m, 1H), 2.20 (m, 1H), 1.84 (m, 1H), 1.65-1.40 (m, 4H); 13C NMR 200.24, 171.31, 155.13, 154.78, 148.41, 146.20, 137.57, 135.47, 129.03, 128.73, 127.31, 109.83, 109.41, 71.61, 64.50, 56.96, 45.98, 25.25, 23.42, 18.70; MS m/z+421.1 (M+Na).

Workup

  1. customthe reaction was quenched with 0.5 ml of methanol
  2. additionThe mixture was diluted with 150 ml of EtAc and 100 ml of 0.2 M HCl
  3. customThe organic solvent layer was separated
  4. customwas separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×80 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on SiO2 chromatography
  10. washeluted with EtAc/hexane (3:2)

Sources & evidence

ORD record
ord-de3fe49c7835457587d7e00b4d582381
Source dataset
uspto-grants-2016_02
Patent number
US09265841B2

Reaction notes

Loading…