Diisobutylaluminumhydride → HCID 69673313, compound

HRID 1426305Notes

Reaction equation

HRID 1426305 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Br:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([CH2:22][N:23]([CH3:25])[CH3:24])[CH:21]=1)[C:15](OC)=[O:16]>O1CCCC1>[Br:11][C:12]1[CH:13]=[C:14]([CH2:15][OH:16])[CH:19]=[C:20]([CH2:22][N:23]([CH3:24])[CH3:25])[CH:21]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 58187962Methyl 3-bromo-5-((dimethylamino)methyl)benzoate

Product 1

HCID 69673313HCID 69673313, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0M Diisobutylaluminum hydride in hexanes (6.2 mL, 6.2 mmol) was added dropwise to a solution of methyl 3-bromo-5-[(dimethylamino)methyl]benzoate (0.50 g, 1.8 mmol, from Step A) in tetrahydrofuran (10 mL) at −78° C. After stirring for 2 hours, the mixture was quenched with saturated potassium sodium tartrate solution and was allowed to warm to room temperature. Ethyl acetate was added and the mixture was then stirred until a biphasic solution formed. The ethyl acetate layer was washed with water (3×), followed by brine, was dried over sodium sulfate and concentrated to give a light yellow oil (0.41 g, 93%). 1H NMR (300 MHz, CDCl3) δ 7.41 (dd, J=1.7 Hz, 1H), 7.37 (dd, J=1.8 Hz, 1H), 7.24 (dd, J=1.4, 0.7 Hz, 1H), 4.65 (s, 2H), 3.37 (s, 2H), 2.22 (s, 6H). LCMS (M+H)+: 244.0, 246.0.

Workup

  1. customthe mixture was quenched with saturated potassium sodium tartrate solution
  2. additionEthyl acetate was added
  3. stirringthe mixture was then stirred until a biphasic solution
  4. customformed
  5. washThe ethyl acetate layer was washed with water (3×)
  6. dry with materialwas dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5c6cbc7db6b24ef280da5eebf9835ace
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

Loading…