Tetrahydrofuran → HCID 67325544, compound

HRID 518140Notes

Reaction equation

HRID 518140 reaction equation
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C1COCC1.C([Si](C(C)C)(C(C)C)[S-])(C)C.[Li+].I[C:40]1[CH:41]=[CH:42][C:43]2[CH:52]3[CH:48]([N:49]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:50][CH2:51]3)[CH2:47][O:46][C:44]=2[CH:45]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][CH:9]([Si:4]([S:5][C:40]1[CH:41]=[CH:42][C:43]2[CH:52]3[CH:48]([N:49]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:50][CH2:51]3)[CH2:47][O:46][C:44]=2[CH:45]=1)([CH:1]([CH3:3])[CH3:2])[CH:6]([CH3:8])[CH3:7])[CH3:11]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 3435097Tris(propan-2-yl)silanethiolHCID 67324624HCID 67324624, compoundHCID 86672977HCID 86672977, compound

Product 1

HCID 67325544HCID 67325544, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

Anhydrous dioxane was sparged with argon gas for 1 h before being used. Triisopropylsilanethiol (0.95 mL, 4.4 mmol) was dissolved into anhydrous 1,4-dioxane (3 mL) and to this 1.0 M lithium hexamethyldisilazide in THF (4.2 mL, 4.2 mmol) was added slowly. The reaction was stirred for 2.5 h. A portion of the lithium triisopropylsilanethiolate solution (2.64, 1.32 mmol) was added to a suspension of tert-butyl 7-iodo-1,3a,4,9b-tetrahydrochromeno[3,4-b]pyrrole-3(2H)-carboxylate P02 (480 mg, 1.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (139 mg, 0.12 mmol) in 1,4-dioxane (2 mL) under argon. The reaction mixture was stirred at 60° C. for 16 h and the solvent was evaporated. The residue was triturated with anhydrous hexane, filtered through a plug of celite, and the filtrate concentrated to yield the crude product which was used in the next step without further purification. MS m/z 408 [M−tBu+H]+.

Workup

  1. customAnhydrous dioxane was sparged with argon gas for 1 h
  2. additionwas added slowly
  3. stirringThe reaction mixture was stirred at 60° C. for 16 h
  4. customthe solvent was evaporated
  5. customThe residue was triturated with anhydrous hexane
  6. filtrationfiltered through a plug of celite
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-bc237c997d934af0bb015d2ba5d83de6
Source dataset
uspto-grants-2015_08
Patent number
US09115147B2

Reaction notes

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