Aluminium lithium hydride → HCID 57794743, compound

HRID 2099291Notes

Reaction equation

HRID 2099291 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C@@:13]2([CH2:25][C:26]#[N:27])[CH2:15][C@H:14]2[CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)C>[C:7]1([C@@:13]2([CH2:25][CH2:26][NH2:27])[CH2:15][C@H:14]2[CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57794777HCID 57794777, compound

Product 1

HCID 57794743HCID 57794743, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

To 18.13 mL 1M lithium aluminum hydride (18.13 mmol) in diethyl ether at 0° C. was added ((1R,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl)cyclopropyl)acetonitrile (5.2 g, 18.13 mmol), accessed via the method of Preparation 22B, dissolved in 20 mL diethyl ether. After complete addition, the reaction mixture was stirred at 0° C. for 3 h. The reaction mixture was diluted with 400 mL diethyl ether and quenched with successive addition of 0.6 mL water, 0.6 mL 15% NaOH, and 3.0 mL water. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated to give the title product (5.1 g, 18.13 mmol 100%) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ 7.29-7.14 (m, 10H), 4.29-4.16 (m, 2H), 3.04-2.99 (m, 1H), 2.91-2.86 (m, 1H), 2.39-2.27 (m, 2H), 1.88-1.83 (m, 1H), 1.28-1.19 (m, 2H), 0.84-0.81 (m, 1H), 0.73-0.71 (m, 1H).

Workup

  1. additionAfter complete addition
  2. customquenched with successive addition of 0.6 mL water, 0.6 mL 15% NaOH, and 3.0 mL water
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3ddacb2b0e3046009321fa08a9e36f35
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

Loading…