Benzhydrylamine → HCID 23111595, compound

HRID 1816947Notes

Reaction equation

HRID 1816947 reaction equation
[OH:1][C:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][C:5](=O)[CH3:6].[CH:10]([NH2:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:10]([NH:23][CH:5]([CH3:6])[CH2:4][CH2:3][C:2]([CH3:9])([OH:1])[CH3:8])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 5049666Sodium triacetoxyborohydrideHCID 110407325-hydroxy-5-methylhexan-2-one

Product 1

HCID 23111595HCID 23111595, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The obtained 5-hydroxy-5-methylhexan-2-one (14.23 g) was dissolved in methylene chloride (520 ml). Thereafter, benzhydrylamine (21.00 g) was added to the solution, and the obtained mixture was stirred at a room temperature overnight. Thereafter, sodium triacetoxy borohydride (46.30 g) was added to the reaction solution, and the obtained mixture was stirred at a room temperature for 4 hours. Thereafter, distilled water (173 ml) was added to the reaction solution, and the obtained solution was then adjusted to be pH 12 by addition of an aqueous 6 M sodium hydroxide solution. After extraction with chloroform, the organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluted with 67% ethyl acetate-hexane) to obtain 5-benzhydrylamino-2-methylhexan-2-ol (22.80 g).

Workup

  1. stirringthe obtained mixture was stirred at a room temperature for 4 hours
  2. distillationThereafter, distilled water (173 ml)
  3. additionwas added to the reaction solution
  4. additionby addition of an aqueous 6 M sodium hydroxide solution
  5. extractionAfter extraction with chloroform
  6. washthe organic layer was washed with a saturated saline solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under a reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (eluted with 67% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ff4b1e3c98ab46229cb97f6d16b9d0c9
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

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