Ammonium Chloride → 1497198-86-3

HRID 1507186Notes

Reaction equation

HRID 1507186 reaction equation
[O:1]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1COCC1>[OH:1][C:2]1([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178491912HCID 178491912, compound

Product 1

HCID 659206591497198-86-3Yield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-oxoazetidine-1-carboxylate (4 g, 23 mmol) in THF (100 mL) at 0° C. was added (4-methoxyphenyl)magnesium bromide (0.5 M in ether) (47 mL, 23 mmol). The reaction mixture was stirred for 3 h, and then a satd. ammonium chloride solution (200 mL) was added. The mixture was extracted with ethyl acetate (200 mL), and the organic layer was separated, dried over Na2SO4, and evaporated under reduced pressure to give a crude product. The product was purified by silica gel chromatography eluting with 25% ethyl acetate in hexane to give tert-butyl 3-hydroxy-3-(4-methoxyphenyl)azetidine-1-carboxylate (2.2 g, 7.64 mmol, 32.7% yield). LCMS (Method 107): m/z 280.7 (M+H) RT=1.929 min; 1H NMR (400 MHz, DMSO-d6) δ 7.39 (d, J=8.8 Hz, 2H), 6.93 (d, J=8.8 Hz, 2H), 6.21 (s, 1H), 4.00 (s, 3H), 3.75 (s, 3H), 1.41 (s, 9H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (200 mL)
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customto give a crude product
  6. customThe product was purified by silica gel chromatography
  7. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c5d8953bdacc47a3b1e79c9910cc0a3c
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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