Sodium Hydroxide → 1-(Diphenylmethyl)azetidin-3-ol

HRID 2075176Notes

Reaction equation

HRID 2075176 reaction equation
[OH-].[Na+].Cl.[CH:4]([N:17]1[CH2:20][CH:19]([OH:21])[CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O>[CH:4]([N:17]1[CH2:20][CH:19]([OH:21])[CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 28017261-benzhydrylazetidin-3-ol Hydrochloride

Product 1

HCID 3304481-(Diphenylmethyl)azetidin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaOH (5N aqueous, 26.1 mL, 131 mmol) was added to a mixture of 1-benzhydrylazetidin-3-ol hydrochloride (30.00 g, 109 mmol) in water (150 mL). The mixture was allowed to stir for 15 min, extracted with AcOEt, dried over MgSO4 to give 1-benzhydrylazetidin-3-ol. 1H NMR (300 MHz, CDCl3) δ ppm 7.35-7.44 (m, 4H), 7.22-7.32 (m, 4H), 7.13-7.22 (m, 2H), 4.40-4.52 (m, 1H), 4.35 (s, 1H), 3.47-3.60 (m, 2H), 2.80-2.97 (m, 2H). MS (ESI) m/z: Calculated; 239.1 Observed: 340.1 (M++1).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-19efa7389ade484abbbd43bcac15bdf7
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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