Triethylamine → tert-Butyl ((1R,3R)-3-cyanocyclopentyl)carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@@H:8]1[CH2:12][CH2:11][C@@H:10]([C:13](=O)[NH2:14])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C@@H:8]1[CH2:12][CH2:11][C@@H:10]([C:13]#[N:14])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
In a round-bottomed flask, ((1R,3R)-3-carbamoyl-cyclopentyl)-carbamic acid tert-butyl ester (96 mg, 0.42 mmol) was suspended in THF (2.5 ml). The reaction mixture was cooled to 0° C. and triethylamine (0.28 ml, 2.01 mmol) followed by trifluoroacetic anhydride (0.095 ml, 0.67 mmol) were added. The homogeneous reaction mixture was stirred at 0° C. for 1.5 h then quenched with water and extracted with dichloromethane (2×). The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford ((1R,3R)-3-cyanocyclopentyl)-carbamic acid tert-butyl ester as an off-white waxy solid which contained some triethylamine trifluoroacetate as a major impurity. This material was used without further purification.
Workup
- additionwere added
- customthen quenched with water
- extractionextracted with dichloromethane (2×)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-db4bddd79d2a41ab8a40b8395b029d12
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
Loading…