Sodium Hydroxide → 2-[4-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]tetrahydropy-ran-4-yl]ethanol

HRID 2223934Notes

Reaction equation

HRID 2223934 reaction equation
FC(F)(F)C(O)=O.[C:8]1([CH3:21])[CH:13]=[CH:12][C:11]([NH:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1.[CH2:22]1[C:27]2([CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:26][CH2:25][O:24][CH:23]1O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1.C(N(CC)CC)C>[C:8]1([CH3:21])[CH:9]=[CH:10][C:11]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:31][CH2:32][C:27]3([CH2:28][CH2:29][OH:30])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH2:17][CH2:16]2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 23020925HCID 23020925, compoundHCID 59714966HCID 59714966, compound

Product 1

HCID 597150012-[4-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]tetrahydropy-ran-4-yl]ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a suspension of 4-(p-toluidino)piperidine trifluoroacetate (synthesized in Preparation Example 4-5) (656 mg) in tetrahydrofuran (5 mL) was added triethylamine (0.44 mL). The solution was stirred at room temperature for 25 minutes. Then, 3,9-dioxaspiro[5.5]undecan-2-ol (synthesized in Example 79) (135 mg) in tetrahydrofuran (3 mL) was added to the solution and it was stirred at room temperature for additional 5 minutes. The reaction solution was ice-cooled and sodium triacetoxyborohydride (333 mg) was added thereto. After allowing the reaction solution for its temperature rise to room temperature, it was stirred for additional 26 hours. To the reaction solution was added a 3N aqueous sodium hydroxide solution (10 mL) and it was extracted with ethyl acetate.

Workup

  1. stirringwas stirred at room temperature for additional 5 minutes
  2. temperaturecooled
  3. customto room temperature
  4. stirringit was stirred for additional 26 hours
  5. extractionwas extracted with ethyl acetate

Sources & evidence

ORD record
ord-e496180ddc434f4fa492cd0d31ffc73e
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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