Diethyl Ether → HCID 67228863, compound

HRID 1807904Notes

Reaction equation

HRID 1807904 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C@@H:10]([NH2:21])[CH2:11][O:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14].[OH-].[Na+].CCOCC>O1CCCC1>[NH2:21][C@@H:10]([CH2:11][O:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[CH2:9][OH:8]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67177747HCID 67177747, compound

Product 1

HCID 67228863HCID 67228863, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (212 mg) in tetrahydrofuran (5 ml) was added a solution of (S)-2-amino-3-(1-phenyl-ethoxy)-propionic acid methyl ester (280 mg) in tetrahydrofuran (5 ml) and the mixture was stirred for 2 hours at room temperature. Sodium hydroxide solution (4N) was added until gas evolution ceased, ether was added and the suspension was filtered through Celite. The solvent was evaporated and the residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/MeOH=90:10) to yield a light yellow liquid, (130 mg, 24%); MS (ISP): 196.1 ((M+H)+).

Workup

  1. filtrationthe suspension was filtered through Celite
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/MeOH=90:10)
  4. customto yield a light yellow liquid, (130 mg, 24%)

Sources & evidence

ORD record
ord-06a758d38eb048119428fb50fae1b829
Source dataset
uspto-grants-2013_01
Patent number
US08357712B2

Reaction notes

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