Diethyl Ether → HCID 178463683, 화합물

HRID 853132노트

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HRID 853132 반응식
[CH2:1]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:24][Si](CC)(CC)CC)([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32](OC(=O)C)(=O)[CH3:33].[NH4+].[Cl-].CCOCC>N1C=CC=CC=1>[CH2:1]([N:8]([CH2:32][CH3:33])[C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]([OH:24])([C:16]([F:18])([F:19])[F:17])[C:20]([F:21])([F:23])[F:22])[CH2:13][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 178477573HCID 178477573, 화합물

생성물 1

HCID 178463683HCID 178463683, 화합물수율 39%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of 200 mg (0.43 mmol) of trans benzyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine (example 3.1) in 2 mL of pyridine was treated with 0.05 mL of acetic acid anhydride (0.51 mmol), stirred overnight at RT and distributed between a saturated aqueous solution of NH4Cl and Et2O. After drying of the combined organic phases over Na2SO4 and evaporation of the solvent, the residue was dissolved in 3.5 mL of THF and treated with 0.86 mL of a 1M BH3-solution in THF. The mixture was stirred at RT for 2 hrs, and the solvent evaporated. The residue was redissolved in THF treated with an excess of TBAF and solution was stirred for 2 hrs. Evaporation of the solvent and chromatography on silica gel with hexane/EtOAc 4:1 gave 64 mg (39%) of trans 2-[4-(benzyl-ethyl-amino)-cyclohexyl]-1,1,1,3,3,3-hexafluoro-propan-2-ol as a light yellow oil, MS: 384 (M+H)+.

후처리

  1. dry with materialAfter drying of the combined organic phases over Na2SO4 and evaporation of the solvent
  2. dissolutionthe residue was dissolved in 3.5 mL of THF
  3. additiontreated with 0.86 mL of a 1M BH3-solution in THF
  4. stirringThe mixture was stirred at RT for 2 hrs
  5. customthe solvent evaporated
  6. dissolutionThe residue was redissolved in THF
  7. additiontreated with an excess of TBAF and solution
  8. stirringwas stirred for 2 hrs
  9. customEvaporation of the solvent and chromatography on silica gel with hexane/EtOAc 4:1

출처 및 근거

ORD 기록
ord-6468c980da9749888ec45b51cd3ee5c5
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253282B2

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