HCID 14304675, compound → HCID 14304678, compound

HRID 414069Notes

Reaction equation

HRID 414069 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]=[C:8]1[C@H:13]([CH2:14][CH2:15][C:16](OC)=[O:17])[O:12][C:11]2[CH:20]=[C:21]3[C:26](=[CH:27][C:10]=2[NH:9]1)[CH2:25][CH2:24][CH2:23][CH2:22]3>O1CCCC1>[OH:17][CH2:16][CH2:15][CH2:14][C@@H:13]1[O:12][C:11]2[CH:20]=[C:21]3[C:26](=[CH:27][C:10]=2[NH:9][C:8]1=[O:7])[CH2:25][CH2:24][CH2:23][CH2:22]3

Participants

4

Reactant 2

HCID 14304675HCID 14304675, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14304678HCID 14304678, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and ice-cooled suspension of lithium aluminum hydride (0.51 g) in dry tetrahydrofuran (20 ml), was added dropwise a solution of methyl (S)-3-(3,4,6,7,8,9-hexahydro-3-oxo-2H-naphtho[2,3-b][1,4]oxazin-2-yl)propionate (1.75 g) in dry tetrahydrofuran (10 ml). The whole was stirred at 0° C. for 1.5 hour and quenched with water. After neutralization with 4N-HCl, the insoluble material was filtered off. The filtrate was extracted with ethyl acetate, and the ethyl acetate layer was washed with water and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (60 g) with ethyl acetate-hexane (3:1, v/v) to yield (S)-6,7,8,9-tetrahydro-2-(3-hydroxypropyl)-2H-naphtho[2,3-b][1,4]oxazin-3(4H)-one as colorless needles (1.56 g, 98.7%), m.p. 139°-140° C. [α]D26 +1.4° (c=0.5, CHCl3).

Workup

  1. temperatureice-cooled
  2. stirringThe whole was stirred at 0° C. for 1.5 hour
  3. customquenched with water
  4. filtrationAfter neutralization with 4N-HCl, the insoluble material was filtered off
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customAfter evaporation of the solvent
  9. customthe residue was purified by column chromatography on silica gel (60 g) with ethyl acetate-hexane (3:1

Sources & evidence

ORD record
ord-232e3c5516ed4c6ea344104c770cb06b
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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