HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium bis(trimethylsilyl)amide → 4-(3-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Reactant | Methyl 4-(3-bromopropyl)benzoate | HCID 10801120 | — |
| Reactant | 5-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one | HCID 12970098 | — |
| Product | 4-(3-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester | HCID 12970099 | 84.2% |
Reaction Steps
Analogous to the procedure described for Compound 1A, Step D, 5-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one (250 mg, 0.602 mmol) was alkylated with NaHMDS (1M in THF, 0.72 mL, 0.72 mmol) and 4-(3-bromo-propyl)-benzoic acid methyl ester (170 mg, 0.663 mmol) to yield 4-(3-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester (300 mg). MS 592.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07414071B2 |
| Source dataset | uspto-grants-2008_08 |
| ORD ID | ord-84be8e1073c34ace95189eba5bd814c3 |
| Source note | uspto-grants-2008_08 |