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

HRID 906347

反応式

HRID 906347 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 over-weekend and then the solvent was removed in vacuo. The residue was diluted with DCM, hexane was added and the resultant precipitate was filtered off. The filtrate was concentrated in vacuo and purified by column 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 was removed in vacuo
  2. additionThe residue was diluted with DCM, hexane
  3. additionwas added
  4. filtrationthe resultant precipitate was filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by column chromatography
  7. washElution with DCM

出典と根拠

ORDレコード
ord-653c2f53d16b4ac2a8f39fa0090f1622
出典データセット
uspto-grants-2011_09
特許番号
US08012981B2

関連ノート

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