Sodium Hydroxide → HCID 63936931, compound

HRID 1045205Notes

Reaction equation

HRID 1045205 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[O:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1.[BH4-].[Na+].[OH-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(OCC)(=O)C.CO>[O:8]1[CH2:13][CH2:12][CH:11]([N:1]2[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]2)[CH2:10][CH2:9]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 79341Piperidin-4-olHCID 121599Tetrahydro-4H-pyran-4-oneHCID 4311764Sodium borohydride

Product 1

HCID 63936931HCID 63936931, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 11026Titanium isopropoxideSolvent

Procedure

Piperidin-4-ol (7.8 g) and dihydro-2H-pyran-4(3H)-one (5.0 g) were dissolved in titanium(IV) isopropoxide (30 mL) and the reaction was stirred at room temperature overnight. Methanol (40 mL) was added and the reaction was cooled to 0°. NaBH4 (3.8 g) was added in several portions over one hour. After two hours 1N aqueous NaOH was added, followed by ethyl acetate addition. After filtration through celite, the layers were seperated, the aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried over Na2SO4. The crude material was purified by column chromatography using CH2Cl2 with 5-10% 7N NH3 in methanol.

Workup

  1. temperaturethe reaction was cooled to 0°
  2. filtrationAfter filtration through celite
  3. customthe layers were seperated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-6d0eb63756254bb98d275a31d07208ef
Source dataset
uspto-grants-2013_10
Patent number
US08563735B2

Reaction notes

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