Sodium Hydroxide → HCID 63936931, compound

HRID 2168398Notes

Reaction equation

HRID 2168398 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 separated, 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% 7NNH3 in methanol.

Workup

  1. temperaturethe reaction was cooled to 0°
  2. filtrationAfter filtration through celite
  3. customthe layers were separated
  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-6e722c0a6d374260a8c62ac187849eee
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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