Aluminium lithium hydride → 2-Amino-3-(perfluoropropyl)-1-phenyl-3-propanol

HRID 1061662Notes

Reaction equation

HRID 1061662 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([NH:15][CH:16]([CH:24]([OH:35])[C:25]([F:34])([F:33])[C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)C1C=CC=CC=1>O1CCCC1>[NH2:15][CH:16]([CH:24]([OH:35])[C:25]([F:33])([F:34])[C:26]([F:31])([F:32])[C:27]([F:28])([F:29])[F:30])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22284257HCID 22284257, compound

Product 1

HCID 222842162-Amino-3-(perfluoropropyl)-1-phenyl-3-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (118 mg) is added to a solution of (2RS,3RS)-2-benzoylamino-4,4,5,5,6,6,6-heptafluoro-3-hydroxy-1-phenylhexane (1.10 g, Reference compound No. 31-2) in anhydrous tetrahydrofuran (20 ml), and the mixture is stirred for three days. The reaction mixture is filtered through Celite to remove impurities. The filtrate is concentrated under reduced pressure, diethyl ether is added to the resulting residue, and the whole is extracted with 0.1 N hydrochloric acid. Sodium hydrogencarbonate is added to the extract to basify the system, and the whole is extracted with ethyl acetate. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure to give the titled reference compound (164 mg).

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. customto remove impurities
  3. concentrationThe filtrate is concentrated under reduced pressure, diethyl ether
  4. additionis added to the resulting residue
  5. extractionthe whole is extracted with 0.1 N hydrochloric acid
  6. additionSodium hydrogencarbonate is added to the
  7. extractionextract
  8. extractionthe whole is extracted with ethyl acetate
  9. washThe extract is washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationThe extract is concentrated under reduced pressure

Sources & evidence

ORD record
ord-795767046d2c40e1ba8d0898a876227a
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

Loading…