Reacción #674292

ord-13b583847d544f91a0835a77a78dda79

Ecuación de reacción

O=C([O-])O.[Na+]
NaHCO3
CC(C)(C)OC(=O)N1CC2(CC(=O)C2)C1
tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate
[BH4-].[Na+]
NaBH4
CC(C)(C)OC(=O)N1CC2(CC(O)C2)C1
tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate
Rendimiento 100.0%

Disolventes

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónThe solution was concentrated by evaporator in vacuo
  2. 2
    Otroto give crude solid
  3. 3
    ExtracciónThe aqueous mixture was extracted with DCM (4×30 mL)
  4. 4
    SecadoThe combined organic solution was dried over anhydrous Na2SO4
  5. 5
    Concentraciónconcentrated by evaporation in vacuo

Procedimiento

To a solution of tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate (507 mg, 2.4 mmol) in MeOH (5.0 mL) was added NaBH4 (182 mg, 4.8 mmol) at 0° C. under N2. It was stirred at 0° C. for 30 min. The solution was concentrated by evaporator in vacuo to give crude solid. A saturated solution of NaHCO3 (30 mL) was added. The aqueous mixture was extracted with DCM (4×30 mL). The combined organic solution was dried over anhydrous Na2SO4 and then concentrated by evaporation in vacuo to afford tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (511 mg, 100%) as a white solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09226923B2uspto-grants-2016_01