Sodium borohydride → HCID 19848717, compound

HRID 1608186Notes

Reaction equation

HRID 1608186 reaction equation
[O:1]=[C:2]1[CH:9]2[CH2:10][N:5]([CH2:6][CH2:7][CH2:8]2)[CH2:4][CH:3]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[BH4-].[Na+]>C(O)C>[OH:1][CH:2]1[CH:9]2[CH2:10][N:5]([CH2:6][CH2:7][CH2:8]2)[CH2:4][CH:3]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12281017HCID 12281017, compound

Product 1

HCID 19848717HCID 19848717, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4-oxo-1-azabicyclo[3.3.1]non-3-yl carboxylate* (22 g, 0.104 moles) in ethanol (200 ml) was cooled in an ice bath to 5° C. and treated portionwise with sodium borohydride (4.0 g). The reaction was then allowed to warm to room temperature and stirred overnight. The solvent was then removed in vacuo, the residue partitioned between dichloromethane (200 ml) and water (75 ml) and the organic layer separated and dried (Na2SO4). Filtration and removal of the solvent afforded the required product as an oil (20.0 g), 85% pure by g.l.c. (OVl, 180° C.) which was used without further purification.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue partitioned between dichloromethane (200 ml) and water (75 ml)
  3. customthe organic layer separated
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and removal of the solvent

Sources & evidence

ORD record
ord-341f34e8947641668fb2998d4bdf62ad
Source dataset
uspto-grants-1989_09
Patent number
US04870081

Reaction notes

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