Borane → HCID 20039805, compound

HRID 1762913Notes

Reaction equation

HRID 1762913 reaction equation
[CH2:1]([O:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[O:6][CH2:7][CH:8]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][N:12]2[C:11](=O)[CH2:10][O:9]1)[CH3:2].B>O1CCCC1.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[O:6][CH2:7][CH:8]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][N:12]2[CH2:11][CH2:10][O:9]1)[CH3:2]

Participants

5

Reactant 2

HCID 6331BoraneHCID 14500457HCID 14500457, compound

Product 1

HCID 20039805HCID 20039805, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

In 300 ml of tetrahydrofuran (freshly distilled from lithium aluminum hydride) was dissolved 1-[(2-ethoxyphenoxy)methyl]-6,7,8,9-tetrahydro-1H-pyrido[2,1-c][1,4]oxazin-4(3H)-one (8.12 g, 0.0265 mole). The solution was cooled to 5° C. in an ice bath and 40 ml of 1M borane in tetrahydrofuran was added by syringe to the stirred solution under nitrogen. The solution was stirred at room temperature for 2 hr and then heated at reflux for 2 hr. The reaction mixture was cooled to room temperature and slowly quenched with glacial acetic acid. The solvent was removed in vacuo. The residue was partitioned between 10% sodium hydroxide and diethyl ether. Removal of the diethyl ether gave a yellow oil. This oil was then dissolved in a minimum amount of chloroform and chromatographed on a 500 g. Silica Gel column (gradient elution with chloroform methanol). Fractions from the column were combined which gave a single spot on TLC (methanol-chloroform) at similar Rf. A total of 5.08 g (65.8%) of a light yellow oil was obtained.

Workup

  1. distillationIn 300 ml of tetrahydrofuran (freshly distilled from lithium aluminum hydride)
  2. temperatureheated
  3. temperatureat reflux for 2 hr
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customslowly quenched with glacial acetic acid
  6. customThe solvent was removed in vacuo
  7. customThe residue was partitioned between 10% sodium hydroxide and diethyl ether
  8. customRemoval of the diethyl ether
  9. customgave a yellow oil
  10. customchromatographed on a 500 g
  11. washSilica Gel column (gradient elution with chloroform methanol)
  12. customgave a single spot on TLC (methanol-chloroform) at similar Rf

Sources & evidence

ORD record
ord-51e58f3b97c2416cbff45d832895e761
Source dataset
uspto-grants-1989_05
Patent number
US04835164

Reaction notes

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