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

HRID 551579

反応式

HRID 551579 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-f82f33f58ceb4348ada8b99912a31ba0
出典データセット
uspto-grants-2011_05
特許番号
US07947718B2

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