Benzylamine → HCID 60128601, compound

HRID 2308184Notes

Reaction equation

HRID 2308184 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCC[CH2:8]1.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[C:23](=[O:40])[CH:24]([OH:39])[C@@H:25]([NH:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:26][CH3:27])C>O>[CH2:12]([NH:19][C:23](=[O:40])[CH:24]([OH:39])[C@@H:25]([NH:28][C:29]([O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:30])[CH:26]([CH3:27])[CH3:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 69831990HCID 69831990, compound

Product 1

HCID 60128601HCID 60128601, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension containing lithium aluminum hydride (1.2 g) and tetrahydrofuran (200 ml) is stirred under reflux for 1.5 hour. The reaction solution is cooled to room temperature, and thereto is added dropwise benzylamine (17.3 g). Then, to the mixture is added dropwise tetrahydrofuran (150 ml) containing (3S)-3-benzyloxycarbonylamino-2-hydroxy-4-methylbutyric acid ethyl ester (10 g), and the mixture is stirred at room temperature for 12 hours. Water is carefully added to the reaction solution, and the mixture is extracted with ethyl acetate. The extract is dried over magnesium sulfate, and the solvent is removed by evaporation under reduced pressure. The residue is purified by silica gel column chromatography [solvent; n-hexane:ethyl acetate (1:1)] to give the desired (1S)-3-benzylamino-1-benzyloxycarbonylamino-1-isopropyl-2-hydroxy-3-oxopropane (9.2 g) as colorless oil.

Workup

  1. temperatureunder reflux for 1.5 hour
  2. stirringthe mixture is stirred at room temperature for 12 hours
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe extract is dried over magnesium sulfate
  5. customthe solvent is removed by evaporation under reduced pressure
  6. customThe residue is purified by silica gel column chromatography [solvent; n-hexane:ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-6361ab98c0964bbf914b2c2a30385942
Source dataset
uspto-grants-2004_12
Patent number
US06835714B1

Reaction notes

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