Triethylamine → (R)-Tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylate

HRID 2382202ノート

反応式

HRID 2382202 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([CH3:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=O>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:22])[C@H:10]([CH3:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 6923226(R)-1-Benzyl-3-methylpiperazine

生成物 1

HCID 10085634(R)-Tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylate収率 85.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (R)-1-benzyl-3-methylpiperazine (10 g, 52.6 mmol) in dichloromethane (30 mL) at room temperature was added triethylamine (10.6 g, 106 mmol) and the reaction mixture was stirred for 1 h. To the reaction mixture was added (BOC)2O (13.7 g, 62.8 mmol) and the contents were stirred for further 4 h. The reaction mixture was quenched in water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product. The crude product was purified by silica gel (100-200 mesh) column chromatography eluting with 10% ethyl acetate in n-hexanes to afford 13.0 g of (R)-tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylate.

後処理

  1. stirringthe contents were stirred for further 4 h
  2. customThe reaction mixture was quenched in water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customThe crude product was purified by silica gel (100-200 mesh) column chromatography
  8. washeluting with 10% ethyl acetate in n-hexanes

出典と根拠

ORDレコード
ord-cda46e477d794b1b897e262014fc7021
出典データセット
uspto-grants-2012_09
特許番号
US08258306B2

反応ノート

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