Triethylamine → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

HRID 423640ノート

反応式

HRID 423640 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]([OH:9])[CH3:8])[CH2:3][CH2:2]1.[O:10](C(OC(C)(C)C)=O)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O.CCN(CC)CC>ClCCCl>[OH:9][CH:7]([CH:4]1[CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:10])[CH2:2][CH2:3]1)[CH3:8]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 3383211-(Piperidin-4-yl)ethan-1-ol

生成物 1

HCID 21989903tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate収率 93%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

(±)-1-(4-Piperidinyl)ethanol (see reference: WO 9725992A, 12.44 g, 65.7 mmol) in 1,2-dichloroethane (500 mL) was stirred at room temperature and BOC2O (14.36 g, 65.8 mmol) was added followed by Et3N (19 mL, 136 mmol). The stirred mixture was heated at gentle reflux for 15 min and then allowed to cool to room temperature and stirred overnight. The solution was washed twice with 10% citric acid, once with 10% Na2CO3, dried over MgSO4, filtered and concentrated to afford (±)-1,1-dimethylethyl 4-(1-hydroxyethyl)-1-piperidinecarboxylate (14 g, 93% yield) as a light amber oil. 1H NMR (400 MHz, DMSO-d6): δ 4.35 (d, 1H, J=4.8 Hz), 3.92 (m, 2H), 3.32 (m, 1H), 2.59 (m, 2H), 1.68 (m, 1H), 1.47 (m, 1H), 1.34 (s, 9H), 1.25 (m, 1H), 1.08-0.88 (m, 2H), 0.97 (d, 3H, J=6.4 Hz).

後処理

  1. temperatureThe stirred mixture was heated
  2. temperatureat gentle reflux for 15 min
  3. washThe solution was washed twice with 10% citric acid, once with 10% Na2CO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8e4caddd4a014e23a176eaaeb99c2806
出典データセット
uspto-grants-2012_01
特許番号
US08101634B2

反応ノート

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