Imidazole → HCID 10267607, compound

HRID 326412Notes

Reaction equation

HRID 326412 reaction equation
[C:1]([C@H:5]1[C@@H:11]([OH:12])[CH2:10][C@H:9]2[N:13]([CH3:14])[C@@H:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].O>CN(C=O)C>[Si:20]([O:12][C@H:11]1[CH2:10][C@H:9]2[N:13]([CH3:14])[C@H:6]([CH2:7][CH2:8]2)[C@H:5]1[C:1]([O:3][CH3:4])=[O:2])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 104904Ecgonine methyl ester

Product 1

HCID 10267607HCID 10267607, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2β-Carbomethoxy-3β-hydroxytropane (304 mg, 1.43 mmol) was dissolved in 4 mL of dry DMF. Imidazole (208 mg, 3.01 mmol) and tert-butyldimethylsilyl chloride (345 mg, 2.29 mmol) were added, and the reaction mixture was stirred overnight. Water was then added, and the mixture was extracted with ether. The combined organic layers were washed with water and brine and dried over MgSO4. The solvent was evaporated in vacuo, and the residue was chromatographed on silica gel half-saturated with ammonia using ethyl acetate as eluent to give 265 mg of the title compound (55% yield): IR (thin film) 2951, 2897, 2857, 1790, 1716, 1497, 1271, 1144, 1107, 837 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 3.91 (dt, 1H, J=11.1, 6.1 Hz), 3.67 (s, 3H), 3.45-3.35 (m, 1H), 3.25-3.17 (m,1H), 2.75-2.68 (m,1H), 2.18 (s, 3H), 2.35- 1.42 (m, 6H), 0.84 (s, 9H), 0.02 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 75.46 MHz) δ 171.4, 64.6, 64.4, 61.6, 54.0, 51.1, 41.2, 39.5, 28.2, 25.8, 25.2, 18.1, 6.6, 6.3; mass spectrum m/z 313 (M+), 256, 242, 182, 97, 82; HRMS (FAB) calcd for C16H32NO3Si (MH ) 314.2143, found 314.2145.

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was chromatographed on silica gel half-saturated with ammonia

Sources & evidence

ORD record
ord-61c7614ec0654367a1a930da39b48132
Source dataset
uspto-grants-1993_12
Patent number
US05268480

Reaction notes

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