Methanol → HCID 86634393, compound

HRID 1191300Notes

Reaction equation

HRID 1191300 reaction equation
C[Si](C=[N+]=[N-])(C)C.[Si:8]([O:25][C@H:26]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@@H:27]1[C:38](OC)=[O:39])([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CO>CCCCCC>[Si:8]([O:25][C@H:26]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@@H:27]1[CH2:38][OH:39])([C:21]([CH3:23])([CH3:24])[CH3:22])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 86634394HCID 86634394, compound

Product 1

HCID 86634393HCID 86634393, compoundYield 207.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

2.0 M of a solution of (trimethylsilyl)diazomethane in hexane (40 mL) was added dropwise to 1-tert-butyl 2-methyl (2S,3S)-3-{[tert-butyl(diphenyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate (11.6 g) and methanol (50 mL) with stirring. The reaction solution was concentrated and the residue was added dimethylformamide (100 mL), tert-butyldiphenylchlorosilane (13.7 mL) and imidazole (6.37 g) and stirred at room temperature for overnight. The reaction solution was added water and extracted with a mixture solution of hexane/ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was added tetrahydrofuran (100 mL), methanol (3 mL) and lithium borohydride (2.51 g) at 0° C. and stirred at room temperature for 1 hour. The reaction solution was added water and aqueous 5% potassium sulfate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→75:25) to obtain the title compound (22.7 g) having the following physical properties.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionthe residue was added dimethylformamide (100 mL), tert-butyldiphenylchlorosilane (13.7 mL) and imidazole (6.37 g)
  3. stirringstirred at room temperature for overnight
  4. additionThe reaction solution was added water
  5. extractionextracted with a mixture solution of hexane/ethyl acetate
  6. washThe extract was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. additionThe residue was added tetrahydrofuran (100 mL), methanol (3 mL) and lithium borohydride (2.51 g) at 0° C.
  10. stirringstirred at room temperature for 1 hour
  11. additionThe reaction solution was added water and aqueous 5% potassium sulfate solution
  12. extractionextracted with ethyl acetate
  13. washThe extract was washed with saturated brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated
  16. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→75:25)

Sources & evidence

ORD record
ord-e3bda20c970742889c863948f232bd7b
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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