Imidazole → HCID 131737104, compound

HRID 60740Notes

Reaction equation

HRID 60740 reaction equation
O[CH:2]([C@H:5]1[O:9][C:8](=[O:10])[CH2:7][CH2:6]1)[CH2:3]C.[C:11]([Si:15](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1.CN([CH:37]=[O:38])C>O>[Si:15]([O:9][CH:5]([CH:6]1[CH2:7][CH2:8][O:10][C:37]1=[O:38])[CH2:2][CH3:3])([C:11]([CH3:14])([CH3:13])[CH3:12])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 121396362HCID 121396362, compound2×

Product 1

HCID 131737104HCID 131737104, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (5S)-5-(1-hydroxypropyl)tetrahydrofuran-2-one (compound 28d, 9 g, 62.5 mmol) in DMF (100 mL) was added tert-butylchlorodiphenylsilane (42.8 g, 156 mmol) and imidazole (10.6 g, 156 mmol) under N2. After being stirred at 50° C. for 12 hours, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine (100 mL) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:20 to 1:3 EtOAc in petroleum ether) to afford 18 g of (5S)-5-[(1-[tert-butyl(diphenyl)silyl]oxypropyl]tetrahydrofuran-2-one. 10 g of the mixture was further purified and separated by SFC to afford 5.6 g of (5S)-5-[(1S)-1-[tert-butyl(diphenyl)silyl]oxypropyl]tetrahydrofuran-2-one (compound 28e-S) and 2 g of (5S)-5-[(1R)-1-[tert-butyl(diphenyl)silyl]oxypropyl]tetrahydrofuran-2-one (compound 28e-R). (Refer to Tetrahedron. 1997, 53, 6281-6294).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine (100 mL)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (eluting with 1:20 to 1:3 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-ff5f4bbff74e4094854044971510a1f9
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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