Ethanolamine → 5-{[4-(2-Azepan-1-yl-ethoxy)-phenyl]-hydroxy-methyl}-6-(2,4,6-trifluoro-phenyl)-naphthalen-2-ol

HRID 1513972노트

반응식

HRID 1513972 반응식
B.C1CN[C@H](C(O)(C2C=CC=CC=2)C2C=CC=CC=2)C1.[N:21]1([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([C:39]3[C:48]4[C:43](=[CH:44][C:45]([OH:49])=[CH:46][CH:47]=4)[CH:42]=[CH:41][C:40]=3[C:50]3[C:55]([F:56])=[CH:54][C:53]([F:57])=[CH:52][C:51]=3[F:58])=[O:38])=[CH:33][CH:32]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(CN)O>C1COCC1.[Cl-].[Na+].O>[N:21]1([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([CH:37]([OH:38])[C:39]3[C:40]([C:50]4[C:55]([F:56])=[CH:54][C:53]([F:57])=[CH:52][C:51]=4[F:58])=[CH:41][CH:42]=[C:43]4[C:48]=3[CH:47]=[CH:46][C:45]([OH:49])=[CH:44]4)=[CH:33][CH:32]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

참가 물질

7

반응물 4

HCID 700EthanolamineHCID 6331BoraneHCID 27248992-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-HCID 67004267[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[6-hydroxy-2-(2,4,6-trifluoro-phenyl)naphthalen-1-yl]-methanone

생성물 1

HCID 670049855-{[4-(2-Azepan-1-yl-ethoxy)-phenyl]-hydroxy-methyl}-6-(2,4,6-trifluoro-phenyl)-naphthalen-2-ol수율 88%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

반응 조건

온도
45 °C

실험 절차

Charge a flask with 1M borane in THF (4 mL) and (R)-(+) α,α-diphenylprolinol (26 mg, 0.1 mmol). Dissolve [4-(2-azepan-1-yl-ethoxy)-phenyl]-[6-hydroxy-2-(2,4,6-trifluoro-phenyl)-naphthalen-1-yl]-methanone (348 mg, 0.7 mmol) in THF (3 mL) and add to the catalyst solution via syringe pump over 1.5 hours at 45° C. Upon completion of the reaction add ethanolamine (0.8 mL, 13.4 mmol) and heat at 45° C. for 2 hours. Cool the reaction to room temperature and add brine (5 mL) and stir for 1 hour. Filter the reaction and separate layers. Dry the organic layer with sodium sulfate, filter and concentrate in vacuo. Purify by silica gel chromatography using a 1.5-5% gradient of methanol in dichloromethane to yield 306 mg (88%) of the title compound: mass spectrum (ion spray) m/z=522 (M+H).

후처리

  1. temperatureCool
  2. customthe reaction to room temperature
  3. filtrationFilter
  4. customthe reaction
  5. customseparate layers
  6. dry with materialDry the organic layer with sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify by silica gel chromatography

출처 및 근거

ORD 기록
ord-f82e2217949f4c9fb29cb26aec1f8ea0
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217032B2

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