Aluminium lithium hydride → HCID 86653879, compound

HRID 533180Notes

Reaction equation

HRID 533180 reaction equation
[N:1]([CH:4]([CH2:12][O:13][CH2:14][O:15][CH3:16])[CH:5]([OH:11])[CH2:6][O:7][CH2:8][O:9][CH3:10])=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:1][CH:4]([CH2:12][O:13][CH2:14][O:15][CH3:16])[C@@H:5]([OH:11])[CH2:6][O:7][CH2:8][O:9][CH3:10]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86653880HCID 86653880, compound

Product 1

HCID 86653879HCID 86653879, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product from Example 1.3 (392 mg, 1.67 mmol) in tetrahydrofuran (10 ml) was added lithium aluminium hydride (1.0M in ether, 3.33 ml) dropwise. The resulting solution was stirred at ambient temperature for 1 hour. The reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate and the aqueous layer evaporated. The residue was triturated with hot ethyl acetate (4×) and the solution evaporated to give the title compound as a colourless oil (261 mg, 75%). 1H NMR (300 MHz, CDCl3) 3.07 (1H, m), 3.38 (3H, s), 3.38 (3H, s), 3.53 (1H, dd, J 6.8, 9.7 Hz), 3.67 (5H, m), 4.64 (2H, s), 4.66 (2H, s); 13C NMR (75 MHz, CDCl3) 52.7, 55.7, 55.7, 70.7, 70.9, 70.9, 97.1, 97.3.

Workup

  1. customThe reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate
  2. customthe aqueous layer evaporated
  3. customThe residue was triturated with hot ethyl acetate (4×)
  4. customthe solution evaporated

Sources & evidence

ORD record
ord-040e7f9427054113a2f9fde98232ad32
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

Loading…