Methyl iodide → HCID 59013445, compound

HRID 1716976Notes

Reaction equation

HRID 1716976 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:47]1[C:42](=[CH:43][C:44]([Cl:57])=[C:45]([CH2:48][C:49]3[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=3)[CH:46]=1)[CH:41]([OH:58])[CH2:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:61]I>C1COCC1>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:47]1[C:42](=[CH:43][C:44]([Cl:57])=[C:45]([CH2:48][C:49]3[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=3)[CH:46]=1)[CH:41]([O:58][CH3:61])[CH2:40]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59013481HCID 59013481, compound

Product 1

HCID 59013445HCID 59013445, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S,3′R,4′S,5′R,6′R)-3′,4′,5′-tris(benzyloxy)-6′-(benzyloxymethyl)-5-chloro-6-(4-ethylbenzyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran]-3-ol (26 mg, 0.032 mmol) in dry THF (0.8 mL) was added NaH (1.5 mg, 0.036 mmol, 60%) and CH3I (3.1 μL, 0.049 mmol) at room temperature. The reaction mixture was stirred for 3 h and quenched by addition of 5 mL of water when TLC showed the reaction was complete. Ethyl acetate (10 mL) was added to the mixture and the organic layer was separated. The aqueous layer was extracted 2× with ethyl acetate (10 mL). The combined organic layers were washed 1× with 10% HCl (10 mL), 2× with water (10 mL), 2× with brine (10 mL) prior to drying over anhydrous Na2SO4. Concentration under reduced pressure and purification of the crude product by prepared TLC provided 22 mg of the pure product.

Workup

  1. customquenched by addition of 5 mL of water when TLC
  2. additionEthyl acetate (10 mL) was added to the mixture
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted 2× with ethyl acetate (10 mL)
  5. washThe combined organic layers were washed 1× with 10% HCl (10 mL), 2× with water (10 mL), 2× with brine (10 mL)
  6. dry with materialto drying over anhydrous Na2SO4
  7. concentrationConcentration
  8. customunder reduced pressure and purification of the crude product
  9. customby prepared TLC

Sources & evidence

ORD record
ord-35526e419702419bb11b1f135e56feaf
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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