Ammonium Chloride → HCID 22618747, compound

HRID 842258Notes

Reaction equation

HRID 842258 reaction equation
[BH4-].[Li+].[C:3]([NH:6][C:7]1([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][CH2:13][O:12][C:10](=[O:11])[CH2:9][CH2:8]1)(=[O:5])[CH3:4].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:3]([NH:6][C:7]([CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH2:8][CH2:9][CH2:10][OH:11])[CH2:14][CH2:13][OH:12])(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 22618900HCID 22618900, compound

Product 1

HCID 22618747HCID 22618747, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of lithium borohydride (220 mg) in tetrahydrofuran (100 ml), under a nitrogen atmosphere, a solution of 4-acetamido-4-(2-phenyl-ethyl)-6-hexanolide (1.4 g) in tetrahydrofuran (30 ml) was dropwise added over 10 minutes and the mixture was further refluxed under heating for 1.5 hours. After cooling, the reaction mixture was neutralized with a saturated aqueous ammonium chloride solution and the solvent was distilled away under reduced pressure. The residue obtained was dissolved in ethyl acetate and the mixture was washed with water and a saturated brine. The mixture was dried over anhydrous magnesium sulfate and the solvent was distilled away to give 3-acetamido-3-(2-phenylethyl)hexane-1,6-diol as a crude product. The product was dissolved in pyridine (20 ml) without purifying, and acetic anhydride (10 ml) was added to the mixture at room temperature. The whole mixture was allowed to stand overnight. The solvent was distilled away under reduced pressure and the residue obtained was purified by silica gel chromatography (eluent; chloroform-ethyl acetate=2:1) to give the subject compound (0.50 g) as a colorless oily substance.

Workup

  1. temperaturethe mixture was further refluxed
  2. temperatureunder heating for 1.5 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue obtained
  6. washthe mixture was washed with water
  7. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-a334e923e0a34e0c863cfef2c94d89a3
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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