Water → tert-Butyl 3-azidopiperidine-1-carboxylate

HRID 341767노트

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HRID 341767 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+].O>CN(C=O)C>[N:19]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[N+:20]=[N-:21]

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 568122N-Boc-3-mesyloxypiperidine

생성물 1

HCID 547722tert-Butyl 3-azidopiperidine-1-carboxylate수율 98.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

A mixture of the title compound of Example 2 (45.1 g, 205 mmol) and NaN3 (39.9 g, 614 mmol, 3.0 eq) in DMF (200 mL) was heated and stirred at 70° C. for 48 h when TLC (solvent system C) indicated the reaction to be complete. The reaction mixture was cooled to rt and poured into cold water (200 mL). The aqueous mixture was extracted with Et2O (500 mL) and the organic extract was back-washed with water (2×100 mL), dried (Na2SO4) and the solvent was evaporated in vacuo to afford the title compound (45.5 g, 98%) as a colorless oil: 1H-NMR (CDCl3) ∂ 3.66-3.80 (m, 1H), 3.57 (m, 1H), 3.45 (m, Japp =4.0 Hz, 1H), 3.12 (m, 2H), 1.90-2.05 (m, 2H), 1.69-1.83 (m, 2H), 1.47 (s, 9H).

후처리

  1. temperaturewas heated
  2. customthe reaction
  3. temperatureThe reaction mixture was cooled to rt
  4. extractionThe aqueous mixture was extracted with Et2O (500 mL)
  5. extractionthe organic extract
  6. washwas back-washed with water (2×100 mL)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-b19525a8a8244751b336250d63eb4920
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856318

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