Tributylvinyltin → HCID 58580729, compound

HRID 1920797Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][CH2:11][C@H:12]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([F:27])[CH:21]=1)[CH3:9].[CH2:36]([Sn](CCCC)(CCCC)C=C)[CH2:37]CC>O1CCOCC1>[Si:29]([O:28][C@@H:12]([CH2:11][O:10][C@@H:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:36]=[CH2:37])[CH3:9])[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([F:27])[CH:21]=1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 100 °C

Procedure

(2S)-1-[(2R)-3-[(1R)-1-(2-Bromophenyl)ethoxy]-2-{[tert-butyl(dimethyl)silyl]oxy}propyl]-2-(3-fluoro-4-methylbenzyl)pyrrolidine (1712 mg, 3.03 mmol), which had been obtained in Example 180 (180b), was dissolved in 1,4-dioxane (30 mL), added with tributyl(vinyl) tin (1.33 mL, 4.55 mL) and tetrakistriphenyl phosphine palladium (347 mg, 0.30 mmol), and stirred for 16 hours at 100° C. After cooling the reaction solution to room temperature, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=4/1) and basic silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a colorless oily substance (1210 mg, yield 78%).

Workup

temperatureAfter cooling the reaction solution to room temperature
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=4/1) and basic silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-6fd6f2fc87f24b4383469e823c757ddc
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173631B2

Reaction notes

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