Sodium Hydroxide → (R)-2-(Methylamino)-2-phenylethanol

HRID 1942905Notes

Reaction equation

HRID 1942905 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10](O)=[O:11].[OH-].[Na+]>O1CCCC1>[CH3:7][NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 681676N-ME-D-PHG-OHHCID 21226445Aluminium lithium hydride

Product 1

HCID 11030005(R)-2-(Methylamino)-2-phenylethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.84 g, 43 mmol) was suspended in 30 ml of tetrahydrofuran and cooled in an ice-bath. A solution of (R)-methylamino-phenyl acetic acid (1.0 g, 6 mmol) in 10 ml of tetrahydrofuran was slowly added over a period of 20 minutes. The resulting mixture was stirred for 1 hour at 0°, 4 hours at room temperature and then refluxed overnight. The mixture was cooled and carefully hydrolysed by addition of 50 ml 15% aqueous sodium hydroxide. Extraction with ethyl acetate gives a crude oil which was purified by chromatography on silica gel using heptane/ethyl acetate 9:1 v/v to give the title compound as a slightly yellowish oil (0.36 g, yield=39%).

Workup

  1. temperaturecooled in an ice-bath
  2. temperaturerefluxed overnight
  3. temperatureThe mixture was cooled
  4. extractionExtraction with ethyl acetate
  5. customgives a crude oil which
  6. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e770350e7b544d7397e6f12e61093fa5
Source dataset
uspto-grants-2013_03
Patent number
US08389717B2

Reaction notes

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