Ammonium Chloride → tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylate

HRID 237287Notes

Reaction equation

HRID 237287 reaction equation
[C:1]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:13][Mg+].[Br-].[NH4+].[Cl-]>CCOCC>[C:4]([O:3][C:1]([N:8]1[CH2:11][C:10]([OH:12])([CH3:13])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178418689HCID 178418689, compound

Product 1

HCID 54751705tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-Boc-azetidin-3-one (3.5 g, 20 mmol) in 50 mL and Et2O was cooled to 0° C. and 3M MeMgBr in Et2O (10 mL, 30 mmol) was added dropwise over 1 h. After 45 min, the reaction was allowed to warm to rt and stir an additional for 18 h. Then ½ sat'd NH4Cl (aq.) was added and the mixture extracted with EtOAc (2×). The combined organic layers were dried and the resulting semisolid was purified by RP HPLC (Agilent) to give the title compound as a white solid (3.2 g, 84%). 1H NMR (CDCl3): 3.84 (q, J=9.2 Hz, 4H), 1.97 (bs, 1H), 1.52 (s, 3H), 1.44 (m, 9H).

Workup

  1. extractionthe mixture extracted with EtOAc (2×)
  2. customThe combined organic layers were dried
  3. customthe resulting semisolid was purified by RP HPLC (Agilent)

Sources & evidence

ORD record
ord-ce9900d3b0ea402798e4bef7d545e7a3
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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