Water → HCID 13079622, compound

HRID 851172Notes

Reaction equation

HRID 851172 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([NH:24][CH2:25][CH:26]([OH:37])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[CH3:23])=[CH:17][CH:16]=1)(OC)=[O:8].O.[OH-].[Na+]>O1CCCC1>[OH:8][CH2:7][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([NH:24][CH2:25][CH:26]([OH:37])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:35])([F:36])[F:34])[CH:28]=2)[CH3:23])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13079632HCID 13079632, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13079622HCID 13079622, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of lithium aluminium hydride (200 mg) in dry tetrahydrofuran (20 ml) was added dropwise, with stirring, a solution of N-[2-(4-(3-carbomethoxypropoxy)phenyl)-1-methylethyl)-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine (800 mg) in dry tetrahydrofuran (30 ml). The mixture was stirred and heated under reflux for 2 hours after which time it was cooled in ice. Water (0.2 ml), 2 M sodium hydroxide (0.2 ml) and water (1 ml) were successively added, the resulting mixture filtered, the tetrahydrofuran dried (magnesium sulphate) and evaporated to leave an oil. Crystallisation from hexane gave N-[2-(4-(4-hydroxybutoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine (450 mg) m.p. 69°-76° as a 45:55 mixture of diastereoisomers.

Workup

  1. stirringThe mixture was stirred
  2. temperatureheated
  3. temperatureunder reflux for 2 hours after which time it
  4. temperaturewas cooled in ice
  5. filtrationthe resulting mixture filtered
  6. dry with materialthe tetrahydrofuran dried (magnesium sulphate)
  7. customevaporated
  8. customto leave an oil
  9. customCrystallisation from hexane

Sources & evidence

ORD record
ord-fa67802ab99446fdbc00a40f6f003696
Source dataset
uspto-grants-1983_05
Patent number
US04382958

Reaction notes

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