Dichloromethane → [1-Benzyl-3-(hydroxymethyl)azetidin-3-YL]methanol

HRID 64368

Reaction equation

HRID 64368 reaction equation
[CH2:1]([N:8]1[CH2:11][C:10]([C:17](OCC)=[O:18])([C:12](OCC)=[O:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(Cl)Cl>CO.[Cl-].[Na+].O>[CH2:1]([N:8]1[CH2:11][C:10]([CH2:12][OH:13])([CH2:17][OH:18])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 11483175Diethyl 1-benzylazetidine-3,3-dicarboxylate

Product 1

HCID 20164320[1-Benzyl-3-(hydroxymethyl)azetidin-3-YL]methanolYield 68.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of diethyl 1-benzylazetidine-3,3-dicarboxylate (4.8 g, 16.5 mmol) in CH3OH (10 mL) was added NaBH4 (1.25 g, 33 mmol). The mixture was stirred at RT for 1 hr. 100 mL of brine and 200 mL of DCM were added. Organic layers were separated from aqueous layers, dried over Na2SO4, concentrated to afford 2.328 g (68%) of (1-benzylazetidine-3,3-diyl)dimethanol as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 7.21-7.31 (m, 5 H), 4.15-4.05 (m, 2 H), 3.48 (d, J=4.8 Hz, 2H), 3.17 (d, J=4.8 Hz, 4 H) and 2.89 (s, 2 H).

Workup

  1. customOrganic layers were separated from aqueous layers
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-050a8bbfbfff4bbf846cecb99f679ab8
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Linked notes

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