Sodium hydride → 1-(Diphenylmethyl)-3-(2-thienylmethoxy)azetidine

HRID 2171985

Reaction equation

HRID 2171985 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+].Cl[CH2:22][C:23]1[S:24][CH:25]=[CH:26][CH:27]=1>CN(C=O)C>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([O:12][CH2:22][C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)[CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 698302-(Chloromethyl)thiopheneHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 671546021-(Diphenylmethyl)-3-(2-thienylmethoxy)azetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-diphenylmethylazetidin-3-ol (359 mg, 1.5 mmol) in DMF (1 mL) at 0° C. under nitrogen was added NaH (60% in oil, 66 mg, 1.65 mmol). The suspension was stirred for 0.5 h at 0° C. then treated with 2-(chloromethyl)thiophene (464 mg, 3.5 mmol; which may be prepared as described in Step 1) dissolved in DMF (2 mL).

Sources & evidence

ORD record
ord-2727df192e7b4ea0bfd48e78ab5e4410
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Linked notes

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