3-Fluorophenol → Tert-butyl 4-(3-fluorophenoxy)piperidine-1-carboxylate

HRID 43346

反応式

HRID 43346 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[F:15][C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:15][C:16]1[CH:21]=[C:20]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 97433-FluorophenolHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 57699520Tert-butyl 4-(3-fluorophenoxy)piperidine-1-carboxylate収率 94.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate (24 g, 112 mmol), 3-fluorophenol (5.6 g, 59 mmol) and triphenylphosphine (31.4 g, 118 mmol) in THF (100 ml) was added di-isopropylazodicarboxylate (23.3 ml, 118 mmol). The reaction was stirred at room temperature for 3 days and then the solvent removed in vacuo. The residue was diluted with DCM, hexane was added and the resultant white precipitate filtered off. The filtrate was concentrated in vacuo and purified by chromatography. Elution with DCM gave the title compound (16.4 g, 87% pure). δH (CDCl3, 250 MHz) 1.47 (9H, s), 1.76 (2H, m), 1.92 (2H, m), 3.35 (2H, ddd), 3.69 (2H, ddd), 4.44 (1H, m), 6.65 (3H, m), 7.20 (1H, m).

後処理

  1. customthe solvent removed in vacuo
  2. additionThe residue was diluted with DCM, hexane
  3. additionwas added
  4. filtrationthe resultant white precipitate filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by chromatography
  7. washElution with DCM

出典と根拠

ORDレコード
ord-93e31a61c21a41989b70d85c7f8821d7
出典データセット
uspto-grants-2013_09
特許番号
US08536182B2

関連ノート

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