Lithium borohydride → HCID 69147839, compound

HRID 747018Notes

Reaction equation

HRID 747018 reaction equation
C([O:4][CH:5]1[C:9]2([CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH2:10]2)[C:8](=[O:25])[O:7][C:6]1([CH3:27])[CH3:26])(=O)C.[BH4-].[Li+]>O1CCCC1>[OH:4][CH:5]([C:9]1([CH2:8][OH:25])[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1)[C:6]([OH:7])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69148927Benzyl 4-(acetyloxy)-3,3-dimethyl-1-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate

Product 1

HCID 69147839HCID 69147839, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 4-(acetyloxy)-3,3-dimethyl-1-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate (from step (i) above; 1.4 g) was dissolved in tetrahydrofuran and lithium borohydride (81 mg) was added. The mixture was heated under reflux for 2 h, cooled and quenched carefully with water and HCl (30 mL, 5N). The mixture was extracted with ethyl acetate and dried (MgSO4), and concentrated in vacuo. The crude product was purified by chromatography on silica using 2-5% methanol in dichloromethane as eluant to afford the product (340 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperaturecooled
  4. customquenched carefully with water and HCl (30 mL, 5N)
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography on silica using 2-5% methanol in dichloromethane as eluant

Sources & evidence

ORD record
ord-29e934fb82b74e38857915dd8f5efa37
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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