Isoamyl Alcohol → (2RS, 3S)-3-carbobenzoxyamino-2-hydroxy-5-methylhexyl isoamyl ether

HRID 1905323Notes

Reaction equation

HRID 1905323 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].[CH2:20]([OH:25])[CH2:21][CH:22]([CH3:24])[CH3:23]>>[CH2:20]([O:25][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])[CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 31260Isoamyl AlcoholHCID 13909433(3S)-3-carbobenzoxyamino-5-methyl-1,2-epoxyhexane

Product 1

HCID 131715982(2RS, 3S)-3-carbobenzoxyamino-2-hydroxy-5-methylhexyl isoamyl ether

Conditions

Temperature
100 °C

Procedure

A mixture of 100 mg of (3S)-3-carbobenzoxyamino-5-methyl-1,2-epoxyhexane, 2 g of dry neutral alumina, and 2 ml of isoamyl alcohol was stirred for 16 hours at 100° C., and then stirred for 90 minutes at 140° C. After filtration of the alumina, the filtrate was evaporated under reduced pressure to obtain 97 mg of (2RS, 3S)-3-carbobenzoxyamino-2-hydroxy-5-methylhexyl isoamyl ether as a colorless oil.

Workup

  1. stirringstirred for 90 minutes at 140° C
  2. filtrationAfter filtration of the alumina
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-830317dd1dd1417abb94cfc1abdc8027
Source dataset
uspto-grants-1989_06
Patent number
US04841067

Reaction notes

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