Aluminium lithium hydride → HCID 67483427, compound

HRID 324866Notes

Reaction equation

HRID 324866 reaction equation
[CH:1]([C:4]1[C:9]([C:10](OCC)=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[C:7]([CH:29]=[CH:30][CH2:31][CH2:32][CH3:33])=[C:6]([CH:34]([CH3:36])[CH3:35])[N:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:17][CH:16]=2)[C:7]([CH:29]=[CH:30][CH2:31][CH2:32][CH3:33])=[C:6]([CH:34]([CH3:35])[CH3:36])[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67483273HCID 67483273, compound

Product 1

HCID 67483427HCID 67483427, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The intermediate obtained in Step C (6 g, 12.35 mmol) was dissolved in anhydrous tetrahydrofuran (“THF”) (130 mL) under argon and treated dropwise at room temperature with lithium aluminum hydride (“LAH”)(1.0M in THF, 24.7 mL, 24.7 mmol). The reaction mixture was stirred at reflux for 3 hr, cooled to room temperature and quenched by the addition of 0.9 mL H2O, 0.9 mL 20% aqueous NaOH, and 2.7 mL H2O. The resulting suspension was filtered through a cake of Celite and the filtrate concentrated and purified by chromatography through silica (20% ethyl acetate/hexane) to afford 4.76 g of the title compound as a colorless wax. 1H NMR (300 MHz, CDCl3): δ 0.73-0.83 (m, 3 H), 1.37-1.70 (m, 14 H), 1.56 (s, 1 H), 1.92 (dq, J=0.90, 6.90 Hz, 2 H), 3.41 (δ, J=6.60, 13.20, 24.60 Hz, 2 H), 4.43 (d, J=5.1 Hz, 2 H), 5.10 (s, 2 H), 5.27-5.37 (m, 1 H), 5.97 (d, J=15.90 Hz, 1 H), 6.97-7.09 (m, 4 H), 7.35-7.48 (m, 5 H).

Workup

  1. temperatureat reflux for 3 hr
  2. customquenched by the addition of 0.9 mL H2O, 0.9 mL 20% aqueous NaOH, and 2.7 mL H2O
  3. filtrationThe resulting suspension was filtered through a cake of Celite
  4. concentrationthe filtrate concentrated
  5. custompurified by chromatography through silica (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-418acd1e57be4a9e8beab7984268ab6c
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

Loading…