Aluminium lithium hydride → HCID 11494564, compound

HRID 1445821Notes

Reaction equation

HRID 1445821 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([CH3:29])=[C:18]([CH2:20][C:21]([N:23]3[CH2:27][CH2:26][CH2:25][C@H:24]3[CH3:28])=O)[N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]([CH3:29])=[C:18]([CH2:20][CH2:21][N:23]3[CH2:27][CH2:26][CH2:25][C@H:24]3[CH3:28])[N:19]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58951437HCID 58951437, compound2×

Product 1

HCID 11494564HCID 11494564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-[2-(4-Benzyloxy-phenyl)-5-methyl-oxazol-4-yl]-1-(2-(R)-methyl-pyrrolidin-1-yl)-ethanone (See Intermediate 18) (0.62 g, 1.6 mmol) in THF (5 mL) at 0° C. is added a solution of lithium aluminum hydride in THF (1 M, 1.6 mL, 1.6 mmol). The cooling bath is removed, and the reaction mixture is allowed to warm to room temperature and stirred for 3.5 h. The reaction is quenched by the sequential addition of water (0.06 mL), 5 N NaOH (0.06 mL), and water (0.18 mL). The mixture is stirred at room temperature overnight and filtered. The solvent is removed in vacuo, and the crude product is obtained (0.49 g, 81%) and used without purification. MS (m/e): 377.2 (M+1)

Workup

  1. customThe cooling bath is removed
  2. customThe reaction is quenched by the sequential addition of water (0.06 mL), 5 N NaOH (0.06 mL), and water (0.18 mL)
  3. stirringThe mixture is stirred at room temperature overnight
  4. filtrationfiltered
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-8dc28378db3c46378b7b83b64134c1ff
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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