Sodium Bicarbonate → 1-Benzhydryl-3-cyclopropylazetidin-3-ol

HRID 2111527Notes

Reaction equation

[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH:6]([N:19]1[CH2:22][C:21](=[O:23])[CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH:6]([N:19]1[CH2:22][C:21]([CH:1]2[CH2:3][CH2:2]2)([OH:23])[CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a 0.5 M cyclopropylmagnesium bromide in THF (4.72 mL, 2.36 mmol), 1-benzhydryl-azetidin-3-one (200 mg, 0.843 mmol) in THF (3 mL) was added dropwise at −78° C. The reaction mixture was stirred at −78° C. for 2 hr. Then it was added saturated NaHCO3 solution and extracted with ether (3×20 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a light yellow oil. The crude product was purified by Prep. HPLC column using CH3CN—H2O-ammonium acetate solvent system. Fractions were collected and concentrated. Then it was extracted with ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated to give a colorless oil as Grignard reaction product. (63 mg, 27% yield).

Workup

extractionextracted with ether (3×20 mL)
dry with materialdried (MgSO4)
concentrationconcentrated
customto give a light yellow oil
customThe crude product was purified by Prep
customFractions were collected
concentrationconcentrated
extractionThen it was extracted with ethyl acetate
dry with materialdried (MgSO4)
concentrationconcentrated
customto give a colorless oil
customas Grignard reaction product

Sources & evidence

ORD record: ord-5886e9e44c2c4cb0bd8c91f4448b96b8
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521442B2

Reaction notes

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