Sodium Hydroxide → HCID 63936931, compound

HRID 624409Notes

Reaction equation

HRID 624409 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. Next day methanol (40 mL) was added and the reaction was cooled to 00. Then NaBH4 (3.8 g) was added in portions over one hour. After two hours 1N aqueous NaOH was added, followed by ethyl acetate addition. After filtration through celite the layers were separated, the aqueous layer extracted with ethyl acetate, and the combined organic layers were dried over Na2SO4. The crude material was purified by column chromatography using CH2Cl2 having 5-10% 7NNH3 in methanol.

Workup

  1. temperaturethe reaction was cooled to 00
  2. filtrationAfter filtration through 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 material was purified by column chromatography

Sources & evidence

ORD record
ord-c259aaf44594435194c3a621cd6dc044
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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