Tetrahydrofuran → tert-Butyl (1S,2S)-1-amino-2-ethylcyclopropane-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([C@:8]1([NH:13]C(OCC[Si](C)(C)C)=O)[CH2:10][C@@H:9]1[CH2:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>CCOC(C)=O>[C:1]([O:5][C:6]([C@:8]1([NH2:13])[CH2:10][C@@H:9]1[CH2:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To the product of Step 3 (3 g, 9 mmol) was added a 1.0 M TBAF solution in THF (9.3 mL, 9.3 mmol) and the mixture heated to reflux for 1.5 h, cooled to rt and then diluted with 500 ml of EtOAc. The solution was successively washed with water (2×100 mL), brine (2×100 mL), dried (MgSO4), concentrated in vacuo to provide the title intermediate
Workup
- temperaturethe mixture heated
- temperatureto reflux for 1.5 h
- washThe solution was successively washed with water (2×100 mL), brine (2×100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5a31458e6ce94b639883b395b5f31015
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07309708B2
Reaction notes
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