Imidazole → (7S,10R)-2-(tert-Butyldimethylsiloxy)-7,8,9,10-tetrahydro-9,9-dimethoxy-7-methyl-10-phenanthridinol

HRID 1457798Notes

Reaction equation

HRID 1457798 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH3:14][O:15][C:16]1([O:33][CH3:34])[C@H:29]([OH:30])[C:28]2[C:19](=[CH:20][N:21]=[C:22]3[C:27]=2[CH:26]=[C:25]([OH:31])[CH:24]=[CH:23]3)[C@@H:18]([CH3:32])[CH2:17]1>CN(C)C=O>[O:31]([C:25]1[CH:24]=[CH:23][C:22]2[C:27](=[C:28]3[C:19](=[CH:20][N:21]=2)[C@@H:18]([CH3:32])[CH2:17][C:16]([O:15][CH3:14])([O:33][CH3:34])[C@@H:29]3[OH:30])[CH:26]=1)[Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57292997(7S,10R)-7,8,9,10-Tetrahydro-9,9-dimethoxy-7-methyl-2,10-phenanthridinediol

Product 1

HCID 11101514(7S,10R)-2-(tert-Butyldimethylsiloxy)-7,8,9,10-tetrahydro-9,9-dimethoxy-7-methyl-10-phenanthridinolYield 91.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Imidazole (1.01 g, 14.8 mmol, 2.60 equiv) and t-butyldimethylsilyl chloride (1.11 g, 7.39 mmol, 1.30 equiv) were added sequentially to a solution of (7S, 10R)-7,8,9,10-tetrahydro-9,9-dimethoxy-7-methyl-2,10-phenanthridinediol (16, 1.64 g, 5.69 mmol, 1 equiv) in N,N-dimethylformamide (10 mL) at 23° C. After stirring for 1 h at 23° C., the reaction mixture was partitioned between water (100 mL) and ethyl acetate (100 mL). The aqueous layer was separated and extracted further with two 100-mL portions of ethyl acetate. The combined organic layers were dried over sodium sulfate and were concentrated. The residue was purified by flash column chromatography (30% ethyl acetate-hexanes) to afford (7S,10R)-2-(tert-butyldimethylsiloxy)-7,8,9,10-tetrahydro-9,9-dimethoxy-7-methyl-10-phenanthridinol (17) as a light yellow foam (2.10 g, 91%).

Workup

  1. customthe reaction mixture was partitioned between water (100 mL) and ethyl acetate (100 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted further with two 100-mL portions of ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationwere concentrated
  6. customThe residue was purified by flash column chromatography (30% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-56ea3c0610e240639f4da7c490632c8e
Source dataset
uspto-grants-1998_12
Patent number
US05849750

Reaction notes

Loading…