Tributylvinyltin → 1-Tert-butyl 2-methyl (2s,4r)-4-[(8-vinylphenanthridin-6-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 1423367Notes

Reaction equation

HRID 1423367 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([O:16][C@H:17]3[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:19]([C:29]([O:31][CH3:32])=[O:30])[CH2:18]3)[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:3]=1.[CH:33]([Sn](CCCC)(CCCC)CCCC)=[CH2:34]>C1(C)C=CC=CC=1.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>[CH:33]([C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([O:16][C@H:17]3[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C@H:19]([C:29]([O:31][CH3:32])=[O:30])[CH2:18]3)[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:3]=1)=[CH2:34]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 594088921-tert-butyl 2-methyl (2S,4R)-4-[(8-bromophenanthridin-6-yl)oxy]pyrrolidine-1,2-dicarboxylate

Product 1

HCID 594088661-Tert-butyl 2-methyl (2s,4r)-4-[(8-vinylphenanthridin-6-yl)oxy]pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a degassed solution of the product mixture from Step 3 (320 mg, 0.64 mmol) in PhMe (5 mL) was added vinyltributyltin (0.225 mL, 0.77 mmol) and tetrakis(triphenylphosphine)palladium (74 mg, 0.06 mmol). The mixture was then heated to reflux for 18 h. The solvent was then removed in vacuo and the crude material was purified on silica (gradient elution, 5-50% EtOAc/hex) to provide the title compound as a 1:1 mixture with the expected regioisomer. LRMS ((M-Boc)+H)+=349.3.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 18 h
  3. customThe solvent was then removed in vacuo
  4. customthe crude material was purified on silica (gradient elution, 5-50% EtOAc/hex)

Sources & evidence

ORD record
ord-7758278365fe4c1f85e6c31be9432da6
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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