tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-((6-methoxypyridin-3-yl)methyl)piperazine-1-carboxylate

HRID 416849ノート

反応式

HRID 416849 の反応式
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([BH3-])#N.[Na+]>C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:21]2[CH2:20][CH2:19][N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH2:23][CH2:22]2)=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 57897155tert-Butyl 4-((6-methoxypyridin-3-yl)methyl)piperazine-1-carboxylate収率 75%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

実験手順

A solution of 6-methoxy-3-pyridine carboxaldehyde (100 mg, 0.73 mmol) in ethanol (2 mL) and acetic acid (0.2 mL) at room temperature was treated with tert-butyl-1-piperazine carboxylate (2.5 eq, 1.82 mmol, 339 mg) and stirred for 5 minutes. Sodium cyanoborohydride (0.95 eq, 0.69 mmol, 44 mg) was added portionwise and the reaction then stirred for 16 h. Concentration in vacuo and preparative tlc purification (EtOAc) gave the product (168 mg, 75%) as a colourless oil; δH (500 MHz, CDCl3) 1.47 (s, 9H, C(CH3)3), 2.00 (s, br, 2H, piperazine NCH2), 2.39 (t, J=4.7 Hz, 2H, piperazine NCH2), 3.43 (t, J=4.9 Hz, 4H, piperazine N(CH2)2), 3.45 (s, 2H, CH2), 3.94 (s, 3H, OCH3), 6.73 (d, J=8.4 Hz, 1H, methoxypyridine H-5), 7.57 (dd, J=8.5, 2.4 Hz, 1H, methoxypyridine H-4), 8.05 (d, br, J=2.3 Hz, 1H, methoxypyridine H-2);

後処理

  1. customthe reaction
  2. stirringthen stirred for 16 h
  3. concentrationConcentration
  4. customin vacuo and preparative tlc purification (EtOAc)

出典と根拠

ORDレコード
ord-601a24a389e8460fa6ac021e6338f933
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

反応ノート

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