Borane → HCID 59803176, compound

HRID 1801595Notes

Reaction equation

HRID 1801595 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([NH:7][C@@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])=O.B>>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][NH:7][C@@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9]

Participants

3

Reactant 2

HCID 6331BoraneHCID 59803164HCID 59803164, compound

Product 1

HCID 59803176HCID 59803176, compoundYield 60.8%

Procedure

To (R)-3-bromo-4-chloro-N-(1-phenylethyl)benzamide 72 (8.15 g, 24.1 mmol) was added borane (130 mL, 129 mmol) (1 M in THF). The reaction mixture was heated to reflux for 3 d, quenched with saturated NaHCO3, and diluted with EtOAc and water. The aqueous phase was extracted with EtOAc (1×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 10% to 40% EtOAc in hexanes) gave (R)—N-(3-bromo-4-chlorobenzyl)-1-phenylethanamine 73 (4.75 g, 60.8% yield) as a colorless oil. Mass spectrum: calculated for C15H15BrClN 323.0. found 324.1 (M++1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 d
  3. customquenched with saturated NaHCO3
  4. additiondiluted with EtOAc and water
  5. extractionThe aqueous phase was extracted with EtOAc (1×)
  6. washthe combined organic extracts were washed with brine (1×)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by flash column chromatography on silica gel (eluted with 10% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d39025466ac44a77b6594f91669593ea
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

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