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

HRID 30455

反応式

HRID 30455 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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-ac96de21ced44c2bb40c40337e69c0cb
出典データセット
uspto-grants-2008_09
特許番号
US07423147B2

関連ノート

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