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

HRID 1846760Notes

Reaction equation

HRID 1846760 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1.[BH4-].[Na+]>C(O)C>[OH:1][CH:2]1[CH2:3][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[CH3:12])[CH2:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23374584tert-Butyl 3-oxocyclobutylcarbamate

Product 1

HCID 22594430tert-Butyl (3-hydroxycyclobutyl)carbamateYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To tert-butyl (3-oxocyclobutyl)carbamate (see PREPARATION 4A, STEP 1; 110 g, 0.594 mol, 1 eq) in ethanol (600 mL) was slowly added sodium borohydride (11.23 g, 0.297 mol, 0.5 eq) at 0° C. Reaction mixture was warmed to RT and stirred at this temperature for 2 h. It was quenched with water (1 L). Solvent was removed under reduced pressure. Water layer was extracted with EtOAc (3×2 L). Combined organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. Residue was purified by column chromatography with aluminum oxide (Eluent: 20% EtOAc in hexane to 10% MeOH in DCM) to get 64 g of tert-butyl (3-hydroxycyclobutyl)carbamate as a white solid in 58% yield.

Workup

  1. customat 0° C
  2. customReaction mixture
  3. customIt was quenched with water (1 L)
  4. customSolvent was removed under reduced pressure
  5. extractionWater layer was extracted with EtOAc (3×2 L)
  6. washCombined organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customResidue was purified by column chromatography with aluminum oxide (Eluent: 20% EtOAc in hexane to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-53d9a2f4bdad4e6292b226c173352f08
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

Loading…