Acetyl chloride → trans-N-(2-hydroxycyclopentyl)acetamide
Reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[OH:7].C(N(CC)CC)C.[C:15](Cl)(=[O:17])[CH3:16]>O1CCCC1>[OH:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][C@H:2]1[NH:1][C:15](=[O:17])[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 30.3 g of trans-2-aminocyclopentanol in 900 ml of tetrahydrofuran under a nitrogen atmosphere was cooled by means of an external ice bath to approximately 10° C. Forty-five milliliters of triethylamine were added followed by the dropwise addition of a solution of 21.3 ml of acetyl chloride in 240 ml of tetrahydrofuran. The resulting mixture was stirred overnight at room temperature. The resulting precipitate was removed by filtration and the filtrate was concentrated in vacuo to provide 43.59 g of the title intermediate as a red oil.
Workup
- customThe resulting precipitate was removed by filtration
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-5270b12e346c431782ec330a4f1fb317
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05141944
Reaction notes
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