Diisobutylaluminum hydride → HCID 71140761, compound

HRID 629924Notes

Reaction equation

HRID 629924 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([CH2:13][CH2:14][C:15](OC)=[O:16])=[CH:10][CH:11]=2)[N:6]([CH3:19])[C:5]1=[O:20].CC(C[AlH]CC(C)C)C.C1COCC1.CCCCCCC>C1COCC1>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:10][CH:11]=2)[N:6]([CH3:19])[C:5]1=[O:20]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 21263495Tetrahydrofuran heptaneHCID 71140765HCID 71140765, compound

Product 1

HCID 71140761HCID 71140761, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 37-1 (0.45 g, 1.40 mmol) in THF (8 mL) chilled to −78° C. was added DIBAL 1.0M in THF heptane (4.22 mL, 4.22 mmol) dropwise. The resulting mixture was stirred at −78° C. for 3 hr, then quench with slow addition of Rochelle's salt solution (3 mL). The resulting mixture was allowed to warm to room temperature, diluted with water and extracted with ethyl acetate. The organic phase was concentrated and flash column separation using a 20-100% ethyl acetate/hexane gradient gave 37-2. (0.22 g, 55%). LRMS (ES) (M+H)+: observed=278.1, calculated=278.4.

Workup

  1. customquench with slow addition of Rochelle's salt solution (3 mL)
  2. temperatureto warm to room temperature
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic phase was concentrated
  6. customflash column separation
  7. customgave 37-2

Sources & evidence

ORD record
ord-08f7816e880f45198b5268492584e5b7
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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