Sodium borohydride → HCID 57495634, compound

HRID 1092354Notes

Reaction equation

HRID 1092354 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=O)[C:14]3([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[N:13]([CH:23]3[CH2:25][CH2:24]3)[C:12]2=[O:26])=[CH:7][CH:6]=1)[CH3:2].[BH4-].[Na+]>C1COCC1.CO>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][C:14]3([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[N:13]([CH:23]3[CH2:25][CH2:24]3)[C:12]2=[O:26])=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 57495633HCID 57495633, compound

Product 1

HCID 57495634HCID 57495634, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 228 mg (0.61 mmol) of 4-(1-Cyclopropyl-2,4-dioxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzoic acid ethyl ester dissolved in 4 ml THF/Methanol 1:1 was added under ice-cooling 70 mg (1.84 mmol) of sodium borohydride. The reaction mixture was stirred for 2 h at RT and then additional 70 mg of sodium borohydride was added and the stirring was continued over night. The whole was concentrated under reduced pressure to dryness and the residue was dissolved in 2 ml of trifluoroacetic acid. To this ice-chilled solution was added again 70 mg of sodium borohydride. The reaction mixture was stirred for 1 h at RT and then the trifluoroacetic acid was removed under reduced pressure. The residue was taken up in EtOAc and washed with sodium bicarbonate solution and water. The crude product was purified by chromatography over silica gel with DCM/EtOAc 9:1 to give 103 mg of pure 4-(1-Cyclopropyl-2-oxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzoic acid ethyl ester. MS (ESI): 357.3 (MH+).

Workup

  1. additionwas added under ice-
  2. waitthe stirring was continued over night
  3. concentrationThe whole was concentrated under reduced pressure to dryness
  4. dissolutionthe residue was dissolved in 2 ml of trifluoroacetic acid
  5. temperatureTo this ice-chilled solution
  6. additionwas added again 70 mg of sodium borohydride
  7. stirringThe reaction mixture was stirred for 1 h at RT
  8. customthe trifluoroacetic acid was removed under reduced pressure
  9. washwashed with sodium bicarbonate solution and water
  10. customThe crude product was purified by chromatography over silica gel with DCM/EtOAc 9:1

Sources & evidence

ORD record
ord-797a927a31fe483196696f0224e9b195
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

Loading…