Benzyl Bromide → 3-(Benzyloxy)-1-(diphenylmethyl)azetidine

HRID 82942

Reaction equation

HRID 82942 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.C(O)(=O)C>[CH2:21]([O:12][CH:10]1[CH2:11][N:8]([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 160894483-(Benzyloxy)-1-(diphenylmethyl)azetidineYield 24.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-diphenylmethylazetidin-3-ol (300 mg, 1.3 mmol) in DMF (2.6 mL) at 0° C. under nitrogen was added NaH (60% in oil, 56 mg, 1.4 mmol). The suspension was stirred for 0.5 h at 0° C. then treated with benzyl bromide (236 μL, 2.0 mmol). The mixture was allowed to warm to room temperature then heated to 80° C. overnight. The reaction mixture was cooled, acetic acid (20 drops) was added and the mixture concentrated under reduced pressure. The crude material was purified on column chromatography (eluent: Pentane/EtOAc, 95/5 to 70/30) to give the product (104 mg, 24%) as an orange oil.

Workup

  1. temperatureto warm to room temperature
  2. temperaturethen heated to 80° C. overnight
  3. temperatureThe reaction mixture was cooled
  4. concentrationthe mixture concentrated under reduced pressure
  5. customThe crude material was purified on column chromatography (eluent: Pentane/EtOAc, 95/5 to 70/30)

Sources & evidence

ORD record
ord-df8f8c4729084f1e89502c2b257a43f8
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Linked notes

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