Lithium borohydride → HCID 57935958, compound

HRID 1434614Notes

Reaction equation

HRID 1434614 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH:27]2[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]2)[CH2:10][C:11](N2[C@H](C3C=CC=CC=3)[C@H](C)N(C)C2=O)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.[BH4-].[Li+]>C1COCC1>[F:8][C:6]1[CH:5]=[C:4]([C@@H:9]([CH:27]2[CH2:28][CH2:29][S:30](=[O:34])(=[O:33])[CH2:31][CH2:32]2)[CH2:10][CH:11]=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57935971HCID 57935971, compound

Product 1

HCID 57935958HCID 57935958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4S,5R)-1-[(3R)-3-(3,5-difluorophenyl)-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)propanoyl]-3,4-dimethyl-5-phenylimidazolidin-2-one (618 mg) in anhydrous THF (15 ml) was added lithium borohydride (1.3 ml of 2M solution in THF). The resulting mixture was heated to 60° C. for 2 hours. The mixture was cooled and quenched with saturated ammonium chloride solution. The mixture was extracted with ethyl acetate (3×50 ml). The organic extracts were dried (MgSO4) and evaporated to a solid to give the title compound, which was used without further purification.

Workup

  1. temperatureThe mixture was cooled
  2. customquenched with saturated ammonium chloride solution
  3. extractionThe mixture was extracted with ethyl acetate (3×50 ml)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customevaporated to a solid

Sources & evidence

ORD record
ord-c41cfc9d17e34a149b23c1bbac33e8d4
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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