Diethyl Ether → HCID 178463683, compound

HRID 853132Notes

Reaction equation

HRID 853132 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 178463683HCID 178463683, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-6468c980da9749888ec45b51cd3ee5c5
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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