4-(Bromoacetyl)benzonitrile → Tert-butyl 1-(2-(4-cyanophenyl)-2-oxoethyl)azetidine-3-carboxylate

HRID 1948504Notes

Reaction equation

HRID 1948504 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[O:4].[NH:13]1[CH2:16][CH:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]1>C1(C)C=CC=CC=1>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([C:3](=[O:4])[CH2:2][N:13]2[CH2:14][CH:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16]2)=[CH:6][CH:7]=1)#[N:10]

Participants

4

Reactant 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 21828700tert-Butyl azetidine-3-carboxylate

Product 1

HCID 66955251Tert-butyl 1-(2-(4-cyanophenyl)-2-oxoethyl)azetidine-3-carboxylateYield 28.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4-(2-bromoacetyl)benzonitrile (448 mg, 2 mmol) in toluene (10 mL) was added tert-butyl azetidine-3-carboxylate (346 mg, 2.2 mmol). The reaction mixture was stirred overnight and then, solvent was removed. The solids were triturated with EtOAC. The solids were collected and dried in vacuo to yield 170 mg of tert-butyl 1-(2-(4-cyanophenyl)-2-oxoethyl)azetidine-3-carboxylate as an off white solid. MS (m+1)=301. HPLC Peak RT=0.97 minutes (Analytical Method B).

Workup

  1. customsolvent was removed
  2. customThe solids were triturated with EtOAC
  3. customThe solids were collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d83773d6cebb4aaa885ba5040bdb862d
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

Loading…