Tetrahydrofuran → tert-Butyl 4-(hydroxymethyl)-4-(pyridin-3-yl)piperidine-1-carboxylate

HRID 391457노트

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HRID 391457 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)([C:14](O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.B.O1CCCC1>CO>[OH:15][CH2:14][C:11]1([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:13][CH2:12]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuranHCID 543822421-(tert-Butoxycarbonyl)-4-(pyridin-3-yl)piperidine-4-carboxylic acid

생성물 1

HCID 58993642tert-Butyl 4-(hydroxymethyl)-4-(pyridin-3-yl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
0 °C

실험 절차

A flask was charged with 1-(tert-butoxycarbonyl)-4-(pyridin-3-yl)piperidine-4-carboxylic acid (4.0 g, 13.1 mmol) and tetrahydrofuran (25 mL). The reaction was placed under nitrogen. To the flask was added borane-tetrahydrofuran complex (1 M in tetrahydrofuran, 26.1 mL, 26.1 mmol) and heated at reflux for 2 h. The reaction was cooled to 0° C. and quenched with methanol (100 mL). The solution was then concentrated in vacuo. The residue was purified via column chromatography (5% methanol/95% dichloromethane) to yield 3.2 g (84%). Mass Spec.: 293.26 (MH)+. LC: tr=1.65 min (Phenomenex-Luna 4.6×50 mm S10, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA Gradient Time=2 min, Flow rate=4 mL/min).

후처리

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. customquenched with methanol (100 mL)
  4. concentrationThe solution was then concentrated in vacuo
  5. customThe residue was purified via column chromatography (5% methanol/95% dichloromethane)
  6. customto yield 3.2 g (84%)

출처 및 근거

ORD 기록
ord-6ecbd9a2c6f240c395de861241088572
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383821B2

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