Water → HCID 178500715, compound

HRID 2091997Notes

Reaction equation

HRID 2091997 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH:5]1[CH2:8][C:7](=[O:9])[CH2:6]1.[BH4-].[Na+].O>CO>[CH3:1][O:2][C:3](=[O:10])[CH2:4][C@H:5]1[CH2:8][C@@H:7]([OH:9])[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57686718Methyl 2-(3-oxocyclobutyl)acetate

Product 1

HCID 178500715HCID 178500715, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3-oxo-cyclobutyl)-acetic acid methyl ester (700 mg, 4.92 mmol) in MeOH (20 ml), NaBH4 (205 mg, 5.41 mmol) is added at 0° C. The mixture is stirred at room temperature for 5 hours. To the mixture, H2O is added and a portion of MeOH is removed under reduced pressure. The mixture is extracted with AcOEt and the organic layer is dried over MgSO4, and concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography to give cis (3-hydroxy-cyclobutyl)-acetic acid methyl ester (578 mg, 80%); TLC (hexane/AcOEt, 1:1) Rf 0.38, 1H NMR (400 MHz, chloroform-d) δ ppm 1.56-1.65 (m, 1H), 1.76 (m, 1H), 2.08-2.16 (m, 2H), 2.44 (d, 2H), 2.51-2.59 (m, 2H), 3.66 (s, 3H), 4.16 (m, 1H).

Workup

  1. customa portion of MeOH is removed under reduced pressure
  2. extractionThe mixture is extracted with AcOEt
  3. dry with materialthe organic layer is dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2c7b120bbc18415fb025e192ff3874a4
Source dataset
uspto-grants-2013_05
Patent number
US08440682B2

Reaction notes

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