1-(Diphenylmethyl)azetidin-3-one → 3-(4-tert-Butylphenyl)-1-diphenylmethyl-3-azetidinol

HRID 2307219Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([Mg]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:13]1([CH:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:20]2[CH2:23][C:22](=[O:24])[CH2:21]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:22]2([OH:24])[CH2:23][N:20]([CH:19]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:21]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 4-tert-butylphenyhnagnesium bromide (11.5 mL, 2.0M (Et2O)) in toluene (50 mL) at −78° C. under argon, was added, dropwise, a solution of 1-diphenylmethyl-3-azetidinone (3) (5.0 g) in toluene (100 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 (3×50 mL). The combined organic fractions were washed (water, brine), dried (Na2SO4) and concentrated in vacuo. Recrystallisation from cyclohexane gave 3-(4-tert-butylphenyl)-1-diphenylmethyl-3-azetidinol (9) (6.23 g), m.p. 168-169° C. (cyclohexane). Found: C. 83.68; H, 7.97; N, 3.72. C26H29NO requires C, 84.06; H, 7.87; N, 3.77%.

Workup

temperaturethen warmed to room temperature
custompartitioned between aqueous ammonium chloride solution (50 mL) and diethyl ether (3×50 mL)
washThe combined organic fractions were washed (water, brine)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customRecrystallisation from cyclohexane

Sources & evidence

ORD record: ord-d010b8260b4b4ad182bba2aded4cb45b
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831078B1

Reaction notes

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