Sodium Hydroxide → 4-((2S)-2-Hydroxy-3-{[1-(3,3,3-trifluoro-propyl)-piperidin-4-ylmethyl]-amino}-propoxy)-9H-fluoren-9-ol

HRID 1634758Notes

Reaction equation

HRID 1634758 reaction equation
[OH:1][CH:2]([CH2:19][NH:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][C:30]([F:33])([F:32])[F:31])[CH2:24][CH2:23]1)[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:18])[C:9]=2[CH:8]=[CH:7][CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[OH:1][C@@H:2]([CH2:19][NH:20][CH2:21][CH:22]1[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][C:30]([F:33])([F:31])[F:32])[CH2:26][CH2:27]1)[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([OH:18])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2×HCID 235535074-(2-Hydroxy-3-{[1-(3,3,3-trifluoro-propyl)-piperidin-4-ylmethyl]-amino}-propoxy)-fluoren-9-one

Product 1

HCID 102765994-((2S)-2-Hydroxy-3-{[1-(3,3,3-trifluoro-propyl)-piperidin-4-ylmethyl]-amino}-propoxy)-9H-fluoren-9-olYield 74.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(2-hydroxy-3-{[1-(3,3,3-trifluoro-propyl)-piperidin-4-ylmethyl]-amino}-propoxy)-fluoren-9-one (0.060 g, 0.13 mmol) in 4 mL THF was treated with LAH (0.010 g, 0.26 mmol) and stirred at ambient temperature overnight. Heated to reflux and cooled. The excess LAH was decomposed by the sequential addition of 0.01 mL of each of water and 1 N NaOH, 0.03 mL of water and 0.5 g Na2SO4. The solids were filtered and the filtrate concentrated in vacuo to give 0.045 g of the title compound as a yellow solid.

Workup

  1. temperatureHeated
  2. temperatureto reflux
  3. temperaturecooled
  4. filtrationThe solids were filtered
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8e8ac1b265014c1c929ac597a4daa765
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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