Bromocyclopentane → 1-Cyclopentylpiperidin-4-ol

HRID 272845ノート

反応式

HRID 272845 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH:14]1(Br)[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[CH:14]1([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

5

反応物 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

生成物 1

HCID 217027851-Cyclopentylpiperidin-4-ol収率 71.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-Hydroxypiperidine (2.08 g, 21.2 mmol), K2CO3 (5.86 g, 2 eq.), cylopentylbromide (11.51 g, 77.6 mmol, 3.7 eq.) and MeOH (20.8 ml) were refluxed together overnight. The reaction was allowed to cool to room temperature and quenched with 2M HCl solution (40 ml) and extracted with TBME (40 ml). The aqueous phase was basified to pH 14 with a 2M NaOH solution and extracted with DCM (4×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give 1-cyclopentyl-4-hydroxypiperidine (2.55 g, 71%) as a pale yellow oil.

後処理

  1. customquenched with 2M HCl solution (40 ml)
  2. extractionextracted with TBME (40 ml)
  3. extractionextracted with DCM (4×50 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. washwashed with DCM
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fc9458b8f94b44a59a393f9bdb1cd505
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

反応ノート

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