Hydrochloric Acid → 3-(4-Cyclopropylmethoxy-phenoxy)-azetidine

HRID 40506Notes

Reaction equation

HRID 40506 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)=[CH:15][CH:14]=2)[CH2:9]1)=O)(C)(C)C.Cl.[OH-].[Na+]>O1CCOCC1>[CH:21]1([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH:10]3[CH2:9][NH:8][CH2:11]3)=[CH:14][CH:15]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866890083-(4-Cyclopropylmethoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866890093-(4-Cyclopropylmethoxy-phenoxy)-azetidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 1.7 g (5.32 mmol) 3-(4-cyclopropylmethoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester in 15 mL 1,4-dioxane is added 12.8 mL (16.0 mmol) HCl in dioxane (1.25 mol/L) and the mixture is stirred for 2 h at rt. 1 N NaOH solution is added until the mixture is slightly basic followed by extraction with DCM (2×). The combined organic layers are washed and dried over MgSO4. The solvent is evaporated and the residue is purified by column chromatography (silica gel; DCM/MeOH; gradient 9:1→7:3) to yield the desired product.

Workup

  1. extractionis slightly basic followed by extraction with DCM (2×)
  2. washThe combined organic layers are washed
  3. dry with materialdried over MgSO4
  4. customThe solvent is evaporated
  5. customthe residue is purified by column chromatography (silica gel; DCM/MeOH; gradient 9:1→7:3)

Sources & evidence

ORD record
ord-9c15b39342a84fbe9d03482d1377794d
Source dataset
uspto-grants-2013_09
Patent number
US08530461B2

Reaction notes

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