Triethylamine → (2R)-3-methyl-2-{[4-(trifluoromethyl)phenyl]amino}butan-1-ol

HRID 1360383노트

반응식

HRID 1360383 반응식
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@@H:10]([C:14](O)=[O:15])[CH:11]([CH3:13])[CH3:12])=[CH:5][CH:4]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1>[CH3:12][CH:11]([CH3:13])[C@@H:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:17])[F:18])=[CH:4][CH:5]=1)[CH2:14][OH:15]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 13388455N-[4-(trifluoromethyl)phenyl]-D-valine

생성물 1

HCID 66968920(2R)-3-methyl-2-{[4-(trifluoromethyl)phenyl]amino}butan-1-ol수율 47%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-[4-(Trifluoromethyl)phenyl]-D-valine (2.15 g, 8.23 mmol) obtained in Step 1 of Example 1 was dissolved in tetrahydrofuran (50 ml), and triethylamine (1.71 mL, 12.3 mmol) and ethyl chloroformate (0.94 mL, 9.88 mmol) were added under cooling. The precipitated salt was filtered off, sodium borohydride (0.62 g, 16.4 mmol) and ice were added, and the mixture was stirred overnight at room temperature. The solvent was evaporated and, after work-up according to a conventional method, the residue was purified by silica gel column chromatography (30% mixed solvent of ethyl acetate/hexane) to give the title compound (0.95 g, 3.84 mmol, 47%).

후처리

  1. temperatureunder cooling
  2. filtrationThe precipitated salt was filtered off
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (30% mixed solvent of ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-b0d618ff56ef4c7cb7eadcdbbf86cff9
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879863B2

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