Acetic Acid → 1-(Oxetan-3-yl)piperidin-4-ol

HRID 921785Notes

Reaction equation

HRID 921785 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1.[O:26]1[CH2:29][C:28](=O)[CH2:27]1>ClCCCl>[O:26]1[CH2:29][CH:28]([N:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)[CH2:27]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 79341Piperidin-4-olHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-Oxetanone

Product 1

HCID 552828561-(Oxetan-3-yl)piperidin-4-olYield 50.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (3.18 g, 15.00 mmol) and acetic acid (0.859 mL, 15.00 mmol) were added to a solution of piperidin-4-ol (1.011 g, 10 mmol) and oxetan-3-one (0.721 g, 10.00 mmol) in DCE (35 mL) and the reaction mixture was stirred at room temperature overnight. Celite was added to the sticky reaction mixture and the reaction mixture was filtered, the filtrate was concentrated in vacuo to give brown oil. The solid was purified by flash chromatography on silica gel using an automated ISCO system (120 g column, eluting with 0-8% 2 N ammonia in methanol/dichloromethane). 1-(oxetan-3-yl)piperidin-4-ol (0.80 g) was obtained as a white solid.

Workup

  1. additionCelite was added to the sticky reaction mixture
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give brown oil
  5. customThe solid was purified by flash chromatography on silica gel using
  6. washan automated ISCO system (120 g column, eluting with 0-8% 2 N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-fdfaa5fd8d2e4a3a95103cf556f0ea12
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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