Lithiumtriethylborohydride → 3-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

HRID 470570Notes

Reaction equation

HRID 470570 reaction equation
C([BH-](CC)CC)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]([N:18]2[CH2:23][CH2:22][C@:21]([CH2:30][C:31]3([CH3:34])[CH2:33][O:32]3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:20][C:19]2=[O:35])[CH3:17])=[C:12]([CH3:36])[CH:11]=1>O1CCCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]([N:18]2[CH2:23][CH2:22][C@:21]([CH2:30][C:31]([OH:32])([CH3:34])[CH3:33])([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:20][C:19]2=[O:35])[CH3:17])=[C:12]([CH3:36])[CH:11]=1

Participants

4

Reactant 2

HCID 23664628LithiumtriethylborohydrideHCID 581023913-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-methyl-oxiranylmethyl)-6-phenyl-[1,3]oxazinan-2-one

Product 1

HCID 581023933-[(S)-1-(4-Bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium triethylborohydride (1 mol/L in tetrahydrofuran, 4.2 mL) was added to an ice-cold solution of 3-[(S)-1-(4-bromo-2-methyl-phenyl)-ethyl]-(S)-6-(2-methyl-oxiranylmethyl)-6-phenyl-[1,3]oxazinan-2-one (1.55 g, ca. 85-90% pure) in tetrahydrofuran (15 mL) at such a rate that the solution temperature remained below 10° C. The resulting solution was stirred in the cooling bath for one more hour and at room temperature for another 2 h. Then, the solution was cooled in an ice bath and the reaction was quenched by the careful addition of water (7 mL). After the addition of aqueous hydrochloric acid and ethyl acetate (80 ml), the organic phase was separated, washed with brine, and dried (MgSO4). The solvent was evaporated to afford the title compound. Yield: 1.48 g (95% of theory); LC-MS (Method 4): tR=4.00 min; Mass spectrum (ESI+): m/z=446/448 (Br) [M+H]+.

Workup

  1. customremained below 10° C
  2. temperatureThen, the solution was cooled in an ice bath
  3. customthe reaction was quenched by the careful addition of water (7 mL)
  4. additionAfter the addition of aqueous hydrochloric acid and ethyl acetate (80 ml)
  5. customthe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9b2334b9781c477da2fcfe9c438ed931
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

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