Acetyl chloride → trans-N-(2-hydroxycyclopentyl)acetamide

HRID 847408Notes

Reaction equation

HRID 847408 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

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10464306rac-(1R,2R)-2-aminocyclopentan-1-ol

Product 1

HCID 14988809trans-N-(2-hydroxycyclopentyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. customThe resulting precipitate was removed by filtration
  2. 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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