Tert-Butylamine → 1-Fluoro-2-methoxy-1-cyclopentanecarboxylic acid tertiary butylamide
Reaction equation
[F:1][C:2]1([C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH:3]1[O:7][CH3:8].C(N(CC)CC)C.C(Cl)(=O)OCC.[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26]>O1CCCC1.O>[C:25]([NH:29][C:9]([C:2]1([F:1])[CH2:6][CH2:5][CH2:4][CH:3]1[O:7][CH3:8])=[O:11])([CH3:28])([CH3:27])[CH3:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
0.4 g (2.7 mmol) of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid in cis form (compound number 12a) disclosed in Example 12 and 0.27 g (2.7 mmol) of triethylamine were dissolved in 10 ml of tetrahydrofuran, and the solution was cooled to 0° C. 0.29 g (2.7 mmol) of ethyl chlorocarbonate was added dropwise, the mixture was stirred at 0° C. for 1 hour, 0.24 g (3.2 mmol) of tertiary butylamine was add, and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ether, and the extract was washed with saturated saline. The ether layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 0.3 g (yield: 55%) of the objective 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid tertiary butylamide in cis form (compound number 29a).
Workup
- stirringthe mixture was further stirred at room temperature for 1 hour
- extractionextracted with ether
- washthe extract was washed with saturated saline
- dry with materialThe ether layer was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled away
Sources & evidence
- ORD record
- ord-a2b8a946512e41d99209bb539af690a5
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05262385
Reaction notes
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