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

HRID 30455

반응식

HRID 30455 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ac96de21ced44c2bb40c40337e69c0cb
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423147B2

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