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

HRID 2173286ノート

反応式

HRID 2173286 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-236ecfce58324480921caf4c5765da9a
出典データセット
uspto-grants-2015_06
特許番号
US09056859B2

反応ノート

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