Water → HCID 178500716, compound

HRID 1966082Notes

Reaction equation

HRID 1966082 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C@H:6]1[CH2:9][C@H:8]([O:10]C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH2:7]1)=[O:4].O.C1COCC1.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C@H:6]1[CH2:9][C@H:8]([OH:10])[CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 178500718HCID 178500718, compound

Product 1

HCID 178500716HCID 178500716, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trans-4-nitro-benzoic acid 3-methoxycarbonylmethyl-cyclobutyl ester (540 mg, 1.84 mmol) in MeOH (20 mL) is added H2O (2.4 mL), THF (10 mL), and K2CO3 (255 mg, 1.84 mmol) at room temperature. The mixture is stirred at room temperature for 45 minutes. The solvent is removed under reduced pressure. Water is added to the obtained residue, and the mixture is extracted with dichloromethane. The organic layer is concentrated under reduced pressure then purified by silica gel column chromatography to give trans-(3-hydroxy-cyclobutyl)-acetic acid methyl ester (230 mg, 87%); TLC (hexane/AcOEt, 1:1) Rf 0.40, 1H NMR (400 MHz, chloroform-) δ ppm 1.69-1.70 (m, 1H), 2.07-2.19 (m, 4H), 2.44-2.46 (d, 2H), 2.41-2.69 (m, 1H), 3.66 (s, 3H), 4.39-4.47 (m, 1H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionWater is added to the obtained residue
  3. extractionthe mixture is extracted with dichloromethane
  4. concentrationThe organic layer is concentrated under reduced pressure
  5. customthen purified by silica gel column chromatography

Sources & evidence

ORD record
ord-352a9fdbac4c431db32016b1977b5d44
Source dataset
uspto-grants-2013_04
Patent number
US08420641B2

Reaction notes

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