1-(Diphenylmethyl)azetidin-3-one → HCID 53767266, compound

HRID 2307221Notes

Reaction equation

HRID 2307221 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[C:10]1([CH:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:17]2[CH2:20][C:19](=[O:21])[CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]2([OH:21])[CH2:20][N:17]([CH:16]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:18]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178418676HCID 178418676, compound

Product 1

HCID 53767266HCID 53767266, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-fluorophenylmagnesium bromide (7.0 mL, 1 .OM (Et2O)) in toluene (20 mL) at −78° C. under argon, was added, dropwise, a solution of 1-diphenylmethyl-3-azetidinone (3) (1.4 g) in toluene (30 mL) over 30 minutes. The mixture was stirred for 4 hours at −78° C. then warmed to room temperature and partitioned between aqueous ammonium chloride solution (50 mL) and diethyl ether (3×20 mL). The combined organic fractions were washed (water, brine), dried (Na2SO4) and concentrated in vacuo. Purification by flash column chromatography (20% ethyl acetate, hexane) gave 3-(4-fluorophenyl)-1-diphenylmethyl-3-azetidinol (15) (1.82 g). To a stirred solution of the free base (1.82 g) in ether (5 mL) was added dropwise a solution of oxalic acid (0.49 g) in acetone (1 mL). The mixture was stirred for 5 minutes then filtered to give the oxalate salt hemihydrate (2.23 g), m.p. 75° C. (acetone). Found: C, 66.71; H. 5.34; N, 3.04. C24H22FNOs.0.5H2O requires C, 66.67; H, 5.32; N, 3.17%.

Workup

  1. temperaturethen warmed to room temperature
  2. custompartitioned between aqueous ammonium chloride solution (50 mL) and diethyl ether (3×20 mL)
  3. washThe combined organic fractions were washed (water, brine)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (20% ethyl acetate, hexane)

Sources & evidence

ORD record
ord-8fd7a632126a4726875fa373381521cb
Source dataset
uspto-grants-2004_12
Patent number
US06831078B1

Reaction notes

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