Boron tribromide → HCID 53977496, compound

HRID 1108771Notes

Reaction equation

HRID 1108771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:25])[CH2:9][NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=3)[CH2:12]2)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:25])[CH2:9][NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)[CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 15887191HCID 15887191, compound

Product 1

HCID 53977496HCID 53977496, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the (1R)-1-(3-chlorophenyl)-2-[3-(3-methoxyphenyl) cyclohexylamino]ethanol (trans-H) obtained in Example 3 (2.21 g) in methylene chloride (100 ml) was cooled to -10° C. After slowly adding dropwise a solution of 1 M boron tribromide in methylene chloride thereto, the mixture was stirred for 2 hours while gradually heating it to room temperature. The reaction solution was poured a portion at a time into an aqueous sodium bicarbonate solution while cooling on ice in order to terminate the reaction, and the extraction was performed with a mixed solvent of chloroform:ethanol=5:1. After washing the organic layer with saturated saline, it was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to produce a crude product which was then separated and purified by silica gel column chromatography (chloroform-chloroform:methanol=20:1) to give 1.72 g of (1R)-1-(3-chlorophenyl)-2-[3-(3-hydroxyphenyl)cyclohexylamino]ethanol (trans-H) (81.1% yield).

Workup

  1. temperaturewhile cooling on ice in order
  2. customto terminate
  3. customthe reaction
  4. extractionthe extraction
  5. washAfter washing the organic layer with saturated saline, it
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto produce a crude product which
  9. customwas then separated
  10. custompurified by silica gel column chromatography (chloroform-chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-857f67aefbd14404ba05e6baee6b7ee0
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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