Hydrochloric Acid → Tert-butyl 3-hydroxy-3-phenylazetidine-1-carboxylate

HRID 540367Notes

Reaction equation

HRID 540367 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:9]=[C:10]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]1.[Cl-].[NH4+].Cl>C(OCC)C.C1COCC1>[OH:9][C:10]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:11][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178418255HCID 178418255, compound

Product 1

HCID 65810524Tert-butyl 3-hydroxy-3-phenylazetidine-1-carboxylateYield 35%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

3.9 ml (11.7 mmol) of a 3M solution of phenylmagnesium bromide in diethyl ether are added dropwise to a solution, immersed in a bath at −50° C., containing 500 mg (2.92 mmol) of 3-oxo-1-(tert-butoxycarbonyl)azetidine in 10 ml of THF. The medium is stirred for 1 hour at −50° C. and hydrolysed by adding a saturated solution of ammonium chloride. After a return to ambient temperature, a 1N solution of hydrochloric acid is added, followed by extraction with ethyl acetate. The organic phase is dried and evaporated to dryness. The crude product obtained is purified on silica in a 7/3 heptane/ethyl acetate mixture. 253 mg in the form of a white powder are obtained with a yield of 35%.

Workup

  1. customimmersed in a bath at −50° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. customThe organic phase is dried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-15dd247a97434eff8f54a1537a212b2c
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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