1-(Diphenylmethyl)azetidin-3-ol → HCID 86703772, compound

HRID 1849894Notes

Reaction equation

HRID 1849894 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[C:21](F)=[CH:22][C:23]([F:33])=[C:24]([CH:32]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].CC(C)([O-])C.[K+]>CS(C)=O>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][C:21]2[C:20]([Cl:19])=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])=[C:23]([F:33])[CH:22]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 23665647Potassium tert-butoxideHCID 58042499tert-butyl 5-chloro-2,4-difluorobenzoate

Product 1

HCID 86703772HCID 86703772, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1-benzhydrylazetidin-3-ol (500 mg, 2.08 mmol), tert-butyl 5-chloro-2,4-difluorobenzoate (568 mg, 2.29 mmol) and potassium tert-butoxide (349 mg, 3.12 mmol) in DMSO (30 mL) was stirred at 20° C. for 1 h. The mixture was quenched with water and extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to get the target compound (700 mg, 72%) which was used in the next step without further purification. LCMS (ESI) m/z: 468.2 [M+H]+.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc (30 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-52b3fa396cb542edbcdd1c731a22cf3e
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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