tert-Butyl piperazine-1-carboxylate → tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

HRID 2173286노트

반응식

HRID 2173286 반응식
[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH:12]=O)[O:7][CH2:6][CH2:5]2.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][N:26]1[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]1)[O:7][CH2:6][CH2:5]2

참가 물질

5

반응물 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 772312476-bromo-5-methoxy-3,4-dihydro-1H-isochromene-1-carbaldehyde

생성물 1

HCID 68433391tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 6-bromo-5-methoxy-3,4-dihydro-1H-isochromene-1-carbaldehyde (230 mg, 0.85 mmol) in 10 mL of DCM was added Boc-piperazine (189 mg, 1.02 mmol) and NaBH(OAc)3 (720 mg, 3.4 mmol), and the mixture was stirred at room temperature overnight. The reaction was diluted with DCM, and washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate.

후처리

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC

출처 및 근거

ORD 기록
ord-236ecfce58324480921caf4c5765da9a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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