Diisobutylaluminum hydride → HCID 117702580, compound

HRID 629919Notes

Reaction equation

HRID 629919 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C@@H:13]([CH3:19])[CH2:14][C:15](OC)=[O:16])=[CH:10][CH:11]=2)[N:6]([CH3:20])[C:5]1=[O:21].CC(C[AlH]CC(C)C)C.C1COCC1.CCCCCCC>C1COCC1>[CH3:22][C:2]([CH3:1])([CH3:23])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C@H:13]([CH2:14][CH2:15][OH:16])[CH3:19])=[CH:10][CH:11]=2)[N:6]([CH3:20])[C:5]1=[O:21]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 21263495Tetrahydrofuran heptaneHCID 71136779HCID 71136779, compound

Product 1

HCID 117702580HCID 117702580, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 36-1 (0.46 g, 1.38 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 (5 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 50-100% ethyl acetate/hexane gradient gave 36-2. (0.26 g, 64%). LRMS (ES) (M+H)+: observed=292.1, calculated=292.4.

Workup

  1. customquench with slow addition of Rochelle's salt solution (5 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 36-2

Sources & evidence

ORD record
ord-e5f63ebf7c9e4770b0602a6d43d807cb
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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