Triethylamine → (1S,5R)-3-(3-{[(1,1-Dimethylethyl)(Dimethyl)Silyl]Oxy}Propyl)-1-[2-Fluoro-4-(Trifluoromethyl)Phenyl]-3-Azabicyclo[3.1.0]Hexane

HRID 254444

반응식

HRID 254444 반응식
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C@:12]12[CH2:17][C@H:16]1[CH2:15][NH:14][CH2:13]2.Br[CH2:19][CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(N(CC)CC)C.N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>C1COCC1>[CH3:28][C:26]([Si:23]([CH3:25])([CH3:24])[O:22][CH2:21][CH2:20][CH2:19][N:14]1[CH2:15][C@H:16]2[C@:12]([C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=3[F:1])([CH2:17]2)[CH2:13]1)([CH3:27])[CH3:29]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 1859152-NaphthylalanineHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 59346768(1S,5R)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

생성물 1

HCID 59759997(1S,5R)-3-(3-{[(1,1-Dimethylethyl)(Dimethyl)Silyl]Oxy}Propyl)-1-[2-Fluoro-4-(Trifluoromethyl)Phenyl]-3-Azabicyclo[3.1.0]Hexane수율 97.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of (1S,5R)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (150 mg, 0.6 mmol), [(3-bromopropyl)oxy](1,1-dimethylethyl)dimethylsilane (233 mg, 0.92 mmol), triethylamine (185 mg, 1.83 mmol) and Nal (20 mg) in THF (2 mL) was stirred at r.t. for 20 h. The reaction mixture was concentrated under vacuum, water was added and the aqueous phase was extracted with EtOAc. The organic phase was dried over Na2SO4 and filtered. The filtrate was concentrated under vacuum and the crude was purified by column chromatography (eluting with EtOAc/cyclohexane 3/7) to give 245 mg of the title compound.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum, water
  2. additionwas added
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. customthe crude was purified by column chromatography (eluting with EtOAc/cyclohexane 3/7)

출처 및 근거

ORD 기록
ord-d661de3d79454f38b7d20a768ef01a40
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875643B2

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