Benzylamine → (3S)-N-benzyl-3-carbobenzoxyamino-2-hydroxy-5-methylhexylamine

HRID 1905330Notes

Reaction equation

HRID 1905330 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]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)C>[CH2:20]([NH:27][CH2:14][CH:13]([OH:15])[C@@H:12]([NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])[CH2:16][CH:17]([CH3:19])[CH3:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 13909433(3S)-3-carbobenzoxyamino-5-methyl-1,2-epoxyhexane

Product 1

HCID 56634722(3S)-N-benzyl-3-carbobenzoxyamino-2-hydroxy-5-methylhexylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 100 mg of (3S)-3-carbobenzoxyamino-5-methyl-1,2-epoxyhexane in 10 ml of diethyl ether were added 2 g of dry silica gel and 0.1 ml of benzylamine, and the mixture was stirred for 16 hours at room temperature, then heated under reflux for 2 hours. After filtration of the silica gel, 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 56 mg of (3S)-N-benzyl-3-carbobenzoxyamino-2-hydroxy-5-methylhexylamine as a colorless viscous oil. To a solution of 54 mg of the amine compound obtained in 10 ml methanol was added 0.2 ml of a 2N-hydrochloric acid. The mixture was hydrogenated over 10 mg of palladium charcoal under hydrogen atmosphere. After filtration of the catalyst, the filtrate was evaporated under reduced pressure to obtain 43 mg of (3S) -N-benzyl-3-amino-2-hydroxy-5-methylhexylamine dihydrochloride.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. filtrationAfter filtration of the silica gel
  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-c447ce8d557047cc936407ae1553d763
Source dataset
uspto-grants-1989_06
Patent number
US04841067

Reaction notes

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