Imidazole → (3aR,4S,5R,6aS)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-5-[(oxan-2-yl)oxy]hexahydro-2H-cyclopenta[b]furan-2-one

HRID 573525Notes

Reaction equation

HRID 573525 reaction equation
CN(C)C=O.[OH:6][CH2:7][C@@H:8]1[C@@H:15]2[C@@H:11]([O:12][C:13](=[O:16])[CH2:14]2)[CH2:10][C@H:9]1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1.N1C=CN=C1.[C:29]([Si:33]([CH3:36])([CH3:35])Cl)([CH3:32])([CH3:31])[CH3:30]>C(O)C>[CH3:35][Si:33]([CH3:36])([C:29]([CH3:32])([CH3:31])[CH3:30])[O:6][CH2:7][C@@H:8]1[C@@H:15]2[C@@H:11]([O:12][C:13](=[O:16])[CH2:14]2)[CH2:10][C@H:9]1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228Dimethylformamide2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 12770849(3aR,4S,5R,6aS)-4-(Hydroxymethyl)-5-[(oxan-2-yl)oxy]hexahydro-2H-cyclopenta[b]furan-2-one

Product 1

HCID 13080724(3aR,4S,5R,6aS)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-5-[(oxan-2-yl)oxy]hexahydro-2H-cyclopenta[b]furan-2-oneYield 105.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a dimethylformamide (hereinafter, abbreviated as DMF in some cases) (100 mL) solution of (3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (50 g), imidazole (29.22 g), and tert-butyldimethylchlorosilane (30.87 g) were sequentially added under ice-cooling, and the mixture was stirred at room temperature for 3.5 hours. After completion of the reaction, a small amount of ethanol was added; the reaction solution was poured into ice water; and this was extracted with ethyl acetate:hexane (2:3). The extract was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution, water and a saturated saline, dried with sodium sulfate, and concentrated under reduced pressure to obtain a titled compound (76.2 g) having the following physical property values.

Workup

  1. additionwere sequentially added under ice-
  2. temperaturecooling
  3. customAfter completion of the reaction
  4. extractionand this was extracted with ethyl acetate:hexane (2:3)
  5. washThe extract was washed with 1N hydrochloric acid
  6. dry with materialan aqueous saturated sodium bicarbonate solution, water and a saturated saline, dried with sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01b8ac3832ff46fc8ae2f92b3f1baf59
Source dataset
uspto-grants-2015_05
Patent number
US09029574B2

Reaction notes

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