Aluminium lithium hydride → 3-Methyl-5-(1-methyl-2(S)-pyrrolidinyl)isoxazole

HRID 21764

Reaction equation

HRID 21764 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[CH:16]=[CH:17][C:18](=[N:20][OH:21])[CH3:19])(OCC1C=CC=CC=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:19][C:18]1[CH:17]=[C:16]([C@@H:12]2[CH2:13][CH2:14][CH2:15][N:11]2[CH3:1])[O:21][N:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 867487371-(1-CBZ-2(S)-pyrrolidinyl)-1-buten-3-one oxime

Product 1

HCID 1193803-Methyl-5-(1-methyl-2(S)-pyrrolidinyl)isoxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The Cbz-protected compound of step 23d is reacted with LAH in THF at 0° C. as described in Example 24 below, and the title compound is isolated in pure form by extraction with ethyl acetate and distillation under high vacuum.

Sources & evidence

ORD record
ord-daec843a89594a82897f91c6ed9e178d
Source dataset
uspto-grants-1995_06
Patent number
US05424444

Linked notes

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