Lithium tritertbutoxyaluminohydride → (5-Hydroxymethyl-pyridin-2-yl)-(4-isopropyl-piperazin-1-yl)-methanone

HRID 30455

Reaction equation

HRID 30455 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]2)=[O:11])=[N:6][CH:5]=1.C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C1COCC1>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:13][CH2:14][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:16][CH2:17]2)=[O:11])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 16684435Lithium tritertbutoxyaluminohydrideHCID 445157746-(4-Isopropyl-piperazine-1-carbonyl)-nicotinic acid methyl ester

Product 1

HCID 44515775(5-Hydroxymethyl-pyridin-2-yl)-(4-isopropyl-piperazin-1-yl)-methanoneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-(4-isopropyl-piperazine-1-carbonyl)-nicotinic acid methyl ester (0.500 g, 1.72 mmol) in THF (15 mL) was cooled to −78° C. in a dry ice bath. A solution of lithium tri-tert-butoxyaluminohydride (1 M in THF, 3.44 mL) was then added drop-wise to the reaction mixture. The resulting solution was allowed to come to rt and was stirred for 18 h. The reaction was quenched with satd. aq. potassium sodium tartrate (Rochelle's salt, 15 mL) and extracted with DCM (3×50 mL). The organic layers were combined, dried (Na2SO4), and concentrated to give the title compound (0.275 g, 61%).

Workup

  1. customto come to rt
  2. customThe reaction was quenched with satd
  3. extractionaq. potassium sodium tartrate (Rochelle's salt, 15 mL) and extracted with DCM (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac96de21ced44c2bb40c40337e69c0cb
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Linked notes

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