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 2036544Notes

Reaction equation

HRID 2036544 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-fd0cc4321c7f4e36b991d2753804575c
Source dataset
uspto-grants-2013_11
Patent number
US08575157B2

Reaction notes

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