Lithium borohydride → HCID 57935988, compound

HRID 1434603Notes

Reaction equation

HRID 1434603 reaction equation
[BH4-].[Li+].[F:3][C:4]1[CH:5]=[C:6]([C@@H:11]([CH:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH2:12][C:13](N2[C@H](C3C=CC=CC=3)[C@H](C)N(C)C2=O)=[O:14])[CH:7]=[C:8]([F:10])[CH:9]=1>C1COCC1>[F:10][C:8]1[CH:7]=[C:6]([C@@H:11]([CH:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[CH2:12][CH:13]=[O:14])[CH:5]=[C:4]([F:3])[CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57936005HCID 57936005, compound

Product 1

HCID 57935988HCID 57935988, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Lithium borohydride (1.5 ml of 2M solution in THF) was added to a solution of (4S,5R)-1-[(3R)-3-(3,5-difluorophenyl)-3-(tetrahydro-2H-pyran-4-yl)propanoyl]-3,4-dimethyl-5-phenylimidazolidin-2-one (882 mg) in anhydrous THF (20 ml) and the mixture was heated to 60° C. for 2 hours. The reaction mixture was cooled and quenched with saturated ammonium chloride and ethyl acetate and stirred for 20 minutes. The organic layer was dried and evaporated to dryness. The residue was purified by chromatography on silica eluting with a gradient of ethyl acetate and isohexane (10:90 to 50:50) to give the title compound as an oil. Yield 345 mg. NMR CDCl3 1.2-1.4 (m, 2H), 1.6-1.85 (m, 4H), 2.15,(m, 1H), 2.5 (m, 1H), 3.25-3.6 (m, 4H), 3.9 (m, 1H), 4.05 (m, 1H), 6.7 (m, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with saturated ammonium chloride and ethyl acetate
  3. customThe organic layer was dried
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography on silica eluting with a gradient of ethyl acetate and isohexane (10:90 to 50:50)

Sources & evidence

ORD record
ord-3d81579e1b1f47c8a7ac69e1e155b339
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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