Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | (Dimethyl sulfide)trihydroboron | HCID 12423031 | — |
| Reactant | HCID 67226198 | HCID 67226198 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67227970 | HCID 67227970 | — |
Reaction Steps
To a solution of EXAMPLE 27D in tetrahydrofuran (3.6 mL) was added borane-methyl sulfide complex (10M in tetrahydrofuran) (0.24 mL). The reaction was heated under reflux for 16 hours, then cooled in an ice/water bath. Methanol (5 mL) was added carefully, and the mixture was stirred cold for 75 minutes. Then 4N HCl in dioxane (0.65 mL) was added and the reaction heated under reflux for 60 minutes. After cooling to room temperature, 1NNH4OH (2.6 mL) was added and the reaction was stirred for 15 minutes. Then the reaction was concentrated, redissolved in methanol, concentrated, redissolved in toluene and concentrated. The crude solids were slurried in CHCl3/methanol, the solids were filtered off, and the filtrate concentrated to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09045420B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-cc7a255ffbaa40d5bba8d6ac47a2675f |
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| Source note | uspto-grants-2015_06 |
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