Lithium tritertbutoxyaluminohydride → (4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone

HRID 551579

Reaction equation

HRID 551579 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12]2)=[O:10])=[N:7][CH:8]=1.COC(=O)[C:23]1[CH:28]=[CH:27][C:26](C(N2CCN(C(C)C)CC2)=O)=[N:25][CH:24]=1.C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C1COCC1>[CH:17]([N:14]1[CH2:15][CH2:16][N:11]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][N:25]3[CH2:26][CH2:27][CH2:28][CH2:23][CH2:24]3)=[CH:8][N:7]=2)=[O:10])[CH2:12][CH2:13]1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 16684435Lithium tritertbutoxyaluminohydrideHCID 445157746-(4-Isopropyl-piperazine-1-carbonyl)-nicotinic acid methyl esterHCID 44515775(5-Hydroxymethyl-pyridin-2-yl)-(4-isopropyl-piperazin-1-yl)-methanone

Product 1

HCID 25126154(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanoneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5-Hydroxymethyl-pyridin-2-yl)-(4-isopropyl-piperazin-1-yl)-methanone. 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-f82f33f58ceb4348ada8b99912a31ba0
Source dataset
uspto-grants-2011_05
Patent number
US07947718B2

Linked notes

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