Lithiumtriethylborohydride → HCID 49838698, compound

HRID 2368046Notes

Reaction equation

HRID 2368046 reaction equation
C([BH-](CC)CC)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH:35]2[CH2:37][CH2:36]2)[N:17]2[CH2:22][CH2:21][C:20]([CH2:29][C:30]3([CH3:33])[CH2:32][O:31]3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:19][C:18]2=[O:34])=[CH:12][CH:11]=1>O1CCCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH:35]2[CH2:37][CH2:36]2)[N:17]2[CH2:22][CH2:21][C:20]([CH2:29][C:30]([OH:31])([CH3:33])[CH3:32])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:19][C:18]2=[O:34])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 23664628LithiumtriethylborohydrideHCID 86667491HCID 86667491, compound

Product 1

HCID 49838698HCID 49838698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium triethylborohydride (1 mol/L in tetrahydrofuran, 4.9 mL) was added to an ice-cold solution of 3-[(4-bromo-phenyl)-cyclopropyl-methyl]-6-(2-methyl-oxiranylmethyl)-6-phenyl-[1,3]oxazinan-2-one (compound processed from diastereomer 2 obtained in Step 3; 1.86 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 3 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 hydrochloric acid and ethyl acetate, the organic phase was separated, washed with brine, and dried (MgSO4). The solvent was evaporated to afford the title compound. Yield: 1.45 g (88% of theory); Mass spectrum (ESI+): m/z=458/460 (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 hydrochloric acid and ethyl acetate
  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-ecf2977464cd442ebcfefb20ec01d0ce
Source dataset
uspto-grants-2014_04
Patent number
US08703765B2

Reaction notes

Loading…