Water → 2-Amino-2-ethylhexan-1-ol

HRID 1376402Notes

Reaction equation

HRID 1376402 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]([CH2:18][CH3:19])([CH2:14][CH2:15][CH2:16][CH3:17])[C:9](OCC)=[O:10].[OH-].[Na+].O>C(OCC)C>[NH2:7][C:8]([CH2:18][CH3:19])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 42614420Ethyl 2-ethylnorleucinate

Product 1

HCID 534210662-Amino-2-ethylhexan-1-olYield 87.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminium hydride (22.22 g) was added to anhydrous diethyl ether (450 ml) under nitrogen. The product from (d) (129.0 g) was diluted with diethyl ether (40 ml) and added dropwise. The reaction was refluxed for 1 hour then cooled to room temperature 1M sodium hydroxide (23 ml) was added dropwise followed by deionised water. The resulting suspension was filtered and the filtrate concentrated to give the desired product as a colourless oil (87.9 g). 1H NMR consistent with the proposed structure.

Workup

  1. additionadded dropwise
  2. temperatureThe reaction was refluxed for 1 hour
  3. additionwas added dropwise
  4. filtrationThe resulting suspension was filtered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d919dd7124d947618811e07e7cd4a8b5
Source dataset
uspto-grants-1997_09
Patent number
US05663165

Reaction notes

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