Sodium Hydroxide → HCID 63936931, compound

HRID 706892Notes

Reaction equation

HRID 706892 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° C. Then NaBH4 (3.8 g) was added in portions over one hour. After 2 hours 1N aqueous NaOH was added, followed by ethyl acetate addition. After filtration though celite the layers were separated, the aqueous layer extracted with ethyl acetate, and the combined organic layers were dried over Na2SO4. The crude was purified by column chromatography using dichloromethane having 5-10% 7N NH3 in methanol.

Workup

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

Sources & evidence

ORD record
ord-1285c4230a934f0d88b9eb39378bce47
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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