N-[tert-Butoxy(hydroxy)methylidene]-3-(trifluoromethyl)phenylalaninato → (S)-b-Amino-3-(trifluoromethyl)benzenepropanol

HRID 339952노트

반응식

HRID 339952 반응식
C(OC([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:10](O)=[O:11])=O)(C)(C)C>O1CCCC1>[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=1)[CH2:10][OH:11]

참가 물질

3

반응물 1

HCID 7020838N-[tert-Butoxy(hydroxy)methylidene]-3-(trifluoromethyl)phenylalaninato

생성물 1

HCID 66635534(S)-b-Amino-3-(trifluoromethyl)benzenepropanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-[3-(trifluoromethyl)phenyl]-propanoic acid (Aldrich) (10.00 g, 30.00 mmol) in tetrahydrofuran (25 mL) with stirring, 1.0 M borane-THF complex in THF (100.0 mL, 100.0 mmol) (newly opened) was added dropwise to keep the internal temperature at 0° C. (release gas, about 15 min). After addition the reaction was stirred at room temperature (rt) for 6 hrs, cooled down with ice-bath, quenched with AcOH:MeOH (1:5, 50 mL), and partitioned between saturated aqueous NaHCO3 and DCM, dried over sodium sulfate, filtered, and evaporated under reduced pressure to give an oil residue, which was purified by combi-flash chromatography to give the desired intermediate. LC-MS found: 320.1 (M+H)+.

후처리

  1. additionwas added dropwise
  2. customat 0° C.
  3. custom(release gas, about 15 min)
  4. additionAfter addition the reaction
  5. temperaturecooled down with ice-bath
  6. customquenched with AcOH:MeOH (1:5, 50 mL)
  7. custompartitioned between saturated aqueous NaHCO3 and DCM
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customto give an oil residue, which
  12. customwas purified by combi-flash chromatography

출처 및 근거

ORD 기록
ord-96cff03cff834f388b9f3d6a9bbe271f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895571B2

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