Methanol → (2RS, 3S)-3-carbobenzoxyamino-2-hydroxy-5-methylhexyl methyl ether

HRID 1905320Notes

Reaction equation

HRID 1905320 reaction equation
[C:1]([NH:11][C@@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH:13]1[O:15][CH2:14]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:20][OH:21]>>[CH3:20][O:21][CH2:14][CH:13]([OH:15])[C@@H:12]([NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH2:16][CH:17]([CH3:18])[CH3:19]

Participants

3

Reactant 2

HCID 887MethanolHCID 13909433(3S)-3-carbobenzoxyamino-5-methyl-1,2-epoxyhexane

Product 1

HCID 13909435(2RS, 3S)-3-carbobenzoxyamino-2-hydroxy-5-methylhexyl methyl ether

Procedure

To a solution of 176 mg of (3S)-3-carbobenzoxyamino-5-methyl-1,2-epoxyhexane in 10 ml of methanol was added 2 g of dry neutral alumina, and the mixture was heated under reflux for 16 hours. After filtration of the alumina, the filtrate was evaporated under reduced pressure. The residue was purified by preparative silica gel thin layer chromatography (developing solvent: lower layer of chloroform/methanol/water=8/3/1 by volume) to obtain 96 mg of (2RS, 3S)-3-carbobenzoxyamino-2-hydroxy-5-methylhexyl methyl ether as a colorless viscous oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. filtrationAfter filtration of the alumina
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by preparative silica gel thin layer chromatography (developing solvent: lower layer of chloroform/methanol/water=8/3/1 by volume)

Sources & evidence

ORD record
ord-0195243b3e794b95aaf51e9fde99fcb2
Source dataset
uspto-grants-1989_06
Patent number
US04841067

Reaction notes

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