Sodium borohydride → tert-Butyl (3-hydroxycyclobutyl)carbamate

HRID 402539Notes

Reaction equation

HRID 402539 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6](=[O:13])[NH:7][CH:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23374584tert-Butyl 3-oxocyclobutylcarbamate

Product 1

HCID 22594430tert-Butyl (3-hydroxycyclobutyl)carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0° C. cold solution of 2.00 g (10.8 mmol) of (3-oxo-cyclobutyl)-carbamic acid tert-butyl ester in 20 mL of ethanol was added portionwise 204 mg (5.40 mmol) of sodium borohydride. The reaction mixture was stirred at room temperature until complete conversion was achieved. The solvent was evaporated, the crude product was taken up in dichloromethane and treated with sat. sodium bicarbonate solution. The phases were separated and the aqueous phase extracted twice with dichloromethane. The organic phases were combined, dried over magnesium sulfate and concentrated to give crude (3-hydroxy-cyclobutyl)-carbamic acid tert-butyl ester. Rt=0.76 min (Method C). Detected mass: 132.2 (M-tBu+H+).

Workup

  1. customThe solvent was evaporated
  2. additiontreated with sat. sodium bicarbonate solution
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted twice with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e1a79594686f43beb73033d6920319f7
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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