1-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid → Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate

HRID 391369

反応式

HRID 391369 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14](O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.B>O1CCCC1>[OH:15][CH2:14][C:11]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9][CH2:10]1

参加物

4

反応物 2

HCID 7369171-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 9994433Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 1-(tert-butoxycarbonyl)-4-phenylpiperidine-4-carboxylic acid (40 g, 131 mmol) in tetrahydrofuran (131 mL) at room temperature was added borane tetrahydrofuran complex (1 M in tetrahydrofuran, 131 mL, 131 mmol). There was effervescence and the substrate quickly went into solution. The reaction was stirred at room temperature for 3 days. The reaction was cooled to 0° C. and quenched by the cautious addition of 1 M sodium hydroxide. The reaction was diluted with ether, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Trituration with 10% EtOAc/Hex (300 mL) gave a white powder which was collected by filtration to give 36.9 g (97%). 1H-NMR (CD3OD, 300 MHz) δ 7.35-7.43 (m, 4H), 7.24-7.26 (m, 1H), 3.78-3.85 (m, 2H), 3.49 (s, 2H), 2.97 (m, 2H), 2.17-2.21 (m, 2H), 1.77-1.87 (m, 2H), 1.46 (s, 9H). Mass spec.: 292.17 (MH)+.

後処理

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched by the cautious addition of 1 M sodium hydroxide
  3. additionThe reaction was diluted with ether
  4. washwashed with water (2×)
  5. dry with materialbrine, dried over magnesium sulfate
  6. concentrationconcentrated
  7. customTrituration with 10% EtOAc/Hex (300 mL) gave a white powder which
  8. filtrationwas collected by filtration
  9. customto give 36.9 g (97%)

出典と根拠

ORDレコード
ord-560281eca67e415f9947ccf8f176167a
出典データセット
uspto-grants-2013_02
特許番号
US08383821B2

関連ノート

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