Sodium borohydride → Benzyl 3-hydroxycyclobutane-1-carboxylate

HRID 2274778Notes

Reaction equation

HRID 2274778 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:7][CH:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5]1>C1COCC1.CO.O>[OH:3][CH:4]1[CH2:7][CH:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 15830669Benzyl 3-oxocyclobutane-1-carboxylate

Product 1

HCID 22934789Benzyl 3-hydroxycyclobutane-1-carboxylateYield 53.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaBH4 (215 mg; 5.68 mmol) was added to the solution of benzyl 3-oxocyclobutanecarboxylate (2.3 g; 11.3 mmol) in THF (30 mL) and MeOH (1.5 mL). The reaction mixture was stirred for 0.5 hour at 0° C., diluted with water (20 mL), and extracted with DCM (50 mL×2). The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and purified by reverse phase flash chromatography to afford 1.24 g (53%) of the title compound as a yellow oil.

Workup

  1. extractionextracted with DCM (50 mL×2)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse phase flash chromatography

Sources & evidence

ORD record
ord-cb05908de8ab46e1822fe3e747ff3f91
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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