Tributyltin Chloride → HCID 71143891, compound
Reaction equation
I[C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[CH2:8][CH2:7][O:6][CH2:5]2.C([Li])CCC.[CH2:16]([Sn:20]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])Cl)[CH2:17][CH2:18][CH3:19]>C1COCC1>[CH2:26]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[CH2:8][CH2:7][O:6][CH2:5]2)[CH2:27][CH2:28][CH3:29]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a cold (−78° C.) mixture of 7-iodo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine (300 mg, 1.205 mmol) and THF (10 mL) was added n-butyllithium (0.530 mL, 1.325 mmol) dropwise under a nitrogen atmosphere. The reaction mixture was stirred at −78° C. for 60 minutes, after which tributylchlorostannane (0.392 mL, 1.445 mmol) was added. The reaction mixture was stirred at −78° C. 60 minutes, then warmed to room temperature and stirred for 1 hour. The reaction was quenched with brine (10 mL) and extracted with EtOAc (2×25 mL). The organic phase was separated, dried over sodium sulfate, concentrated, and purified via flash column chromatography to give the title compound as an oil, which was used without further purification (300 mg, 60%).
Workup
- stirringThe reaction mixture was stirred at −78° C
- temperature60 minutes, then warmed to room temperature
- stirringstirred for 1 hour
- customThe reaction was quenched with brine (10 mL)
- extractionextracted with EtOAc (2×25 mL)
- customThe organic phase was separated
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- custompurified via flash column chromatography
Sources & evidence
- ORD record
- ord-f4cbdfed318d426c96ed76e62eea3b06
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056873B2
Reaction notes
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