Diisopropylethylamine → (2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one
Reaction equation
[CH2:1]([O:4][NH:5][C@@H:6]1[CH:11]=[CH:10][C@@H:9]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[NH:8][CH2:7]1)[CH:2]=[CH2:3].C(N(C(C)C)C(C)C)C.[C:30](=O)(OC(Cl)(Cl)Cl)[O:31]C(Cl)(Cl)Cl>C(#N)C>[CH2:1]([O:4][N:5]1[C:30](=[O:31])[N:8]2[CH2:7][C@H:6]1[CH:11]=[CH:10][C@H:9]2[CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[CH:2]=[CH2:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of O-allyl-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)hydroxylamine (Intermediate 128, 2.0 g, 6.70 mmol) in acetonitrile (560 mL), N-ethyl-N-isopropylpropan-2-amine (4.67 ml, 26.80 mmol) was added. Bis(trichloromethyl) carbonate (0.795 g, 2.68 mmol) dissolved in 40 mL CH3CN was added via a syringe pump (at a rate 0.1 ml/min) at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. It was then allowed to stir at room temperature overnight. The mixture was then concentrated and diluted with EtOAc (50 mL). The organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column (12 g, 0-25% Hex/EA) to give the desired product as a colorless oil (1.64 g).
Workup
- additionwas added via a syringe pump (at a rate 0.1 ml/min) at 0° C
- stirringto stir at room temperature overnight
- concentrationThe mixture was then concentrated
- additiondiluted with EtOAc (50 mL)
- washThe organic layer was washed with water, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel column (12 g, 0-25% Hex/EA)
Sources & evidence
- ORD record
- ord-f86c167064fd4865b7141b679157ba25
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309245B2
Reaction notes
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