Imidazole → (3aR,4R,5R,6aS)-5-Benzoyloxy-4-[(t-butyldiphenylsiloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one

HRID 480216Notes

Reaction equation

HRID 480216 reaction equation
[C:1]([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@@H:11]1[CH2:19][OH:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:26]([Si:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)Cl)([CH3:29])([CH3:28])[CH3:27].[Cl-].[NH4+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@@H:11]1[CH2:19][O:20][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 7156973(3aR,4R,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Product 1

HCID 22951116(3aR,4R,5R,6aS)-5-Benzoyloxy-4-[(t-butyldiphenylsiloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-oneYield 83.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2 (2.40 g, 8.8 mmol), 4-(dimethylamino)pyridine (100 mg, 0.82 mmol), and imidazole (1.00 g, 14.7 mmol) in methylene chloride (35 mL) was added dropwise t-butyldiphenylchlorosilane (2.85 g, 10.4 mmol). After stirring overnight, the mixture was added to saturated ammonium chloride (40 mL), extracted with ethyl acetate (3×40 mL), dried (magnesium sulfate), filtered, concentrated, and chromatographed on a 14 cm tall×53 mm diameter silica gel eluting with 30% ethyl acetate in hexane to afford 3 (3.776 g, 83%).

Workup

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on a 14 cm tall×53 mm

Sources & evidence

ORD record
ord-bb78205619eb437cbe5e0e50a43663f3
Source dataset
uspto-grants-2003_11
Patent number
US06649655B2

Reaction notes

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