HCID 11423959, compound → HCID 68937587, compound

HRID 388748Notes

Reaction equation

HRID 388748 reaction equation
[Si:1]([O:8][C@H:9]1[C:14](=[CH2:15])[C@H:13]([CH2:16][OH:17])[CH2:12][C@H:11]([OH:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si:19](C1NC=CN=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>ClCCl>[Si:1]([O:8][C@H:9]1[C:14](=[CH2:15])[C@H:13]([CH2:16][O:17][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:12][C@H:11]([OH:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11423959HCID 11423959, compoundHCID 68937051HCID 68937051, compound

Product 1

HCID 68937587HCID 68937587, compoundYield 115.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound of Example 16H (574 mg, 2.1 mmol) was dissolved in 35 mL of dichloromethane and tert-butyldimethylsilylimidazole (0.54 mL, 2.8 mmol) was added. After stirring overnight, the reaction was diluted with dichloromethane and washed twice with 10% NaCl, then dried over MgSO4, filtered and concentrated in vacuo. After a second run using 340 mg of the starting diol, the combined unpurified product mixtures were purified by silica gel chromatography (200 mL of SiO2, elution with a gradient of 1:4 ethyl acetate:hexanes to ethyl acetate) to afford the titled compound (940 mg) contaminated with a small amount of a regioisomeric bis-TBS ether.

Workup

  1. washwashed twice with 10% NaCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customwere purified by silica gel chromatography (
  6. wash200 mL of SiO2, elution with a gradient of 1:4 ethyl acetate

Sources & evidence

ORD record
ord-2fb0dc3b4fef4b429e501140cc6a2839
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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