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

HRID 2249205Notes

Reaction equation

HRID 2249205 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-09b86caf8ed54de3b03eb393a8b97dce
Source dataset
uspto-grants-1991_08
Patent number
US05043341

Reaction notes

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