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N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2) → Tert-butyl 4-[(benzyloxy)methyl]-3-fluoro-4-hydroxypiperidine-1-carboxylate

HRID 70789
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HRID 70789 반응식
[F:1][H-]F.[K+].CCCC[N+](CCCC)(CCCC)CCCC.F.F.[F-].[CH2:25]([O:32][CH2:33][C:34]12[O:40][CH:39]1[CH2:38][N:37]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:36][CH2:35]2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)(Cl)Cl>[CH2:25]([O:32][CH2:33][C:34]1([OH:40])[CH2:35][CH2:36][N:37]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:38][CH:39]1[F:1])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
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참가 물질

5

반응물 3

HCID 11748636N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2)HCID 86677053Tert-butyl 6-[(benzyloxy)methyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylateHCID 178506425HCID 178506425, 화합물

생성물 1

HCID 71268614Tert-butyl 4-[(benzyloxy)methyl]-3-fluoro-4-hydroxypiperidine-1-carboxylate수율 66.3%

시약·촉매·용매 1

HCID 6212
Chloroform
용매

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온도
120 °C

실험 절차

Potassium bifluoride (1.22 g) and tetrabutylammonium dihydrogentrifluoride (472 mg) were added to tert-butyl 6-[(benzyloxy) methyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (2.50 g), followed by heating and stirring at 120° C. for 2 days. The reaction was diluted with chloroform and filtered through Celite. The residue obtained by concentration of the solvent under reduced pressure was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 4-[(benzyloxy)methyl]-3-fluoro-4-hydroxypiperidine-1-carboxylate (1.76 g).

후처리

  1. temperatureby heating
  2. filtrationfiltered through Celite
  3. customThe residue obtained by concentration of the solvent under reduced pressure
  4. customwas purified by silica gel column chromatography (EtOAc/hexane)

출처 및 근거

ORD 기록
ord-50961c977c3c40c8a5ece1e330f477df
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822688B2

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