Acetic Anhydride → Tert-butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate

HRID 643541Notes

Reaction equation

HRID 643541 reaction equation
[OH:1][CH:2]([C:4]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7][C:6]([O:11][CH3:12])([O:9][CH3:10])[CH2:5]1)[CH3:3].C(N(CC)CC)C.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:27]([O:1][CH:2]([C:4]1([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:8][CH2:7][C:6]([O:11][CH3:12])([O:9][CH3:10])[CH2:5]1)[CH3:3])(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 57880496Tert-butyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclopentanecarboxylate

Product 1

HCID 68534118Tert-butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclopentanecarboxylate (8.64 g, 31.5 mmol) in 100 mL of DCM was treated with triethylamine (8.78 mL, 63.0 mmol) followed by acetic anhydride (5.94 mL, 63.0 mmol). Then DMAP (˜200 mg) was added and the resulting mixture was stirred at rt overnight. The reaction mixture was diluted with DCM, washed twice with 1N HCl solution, once with saturated NaHCO3 solution, and once with brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. Purification by flash chromatography (silica, 20% ethyl acetate/hexanes) provided tert-butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate.

Workup

  1. washwashed twice with 1N HCl solution, once with saturated NaHCO3 solution
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (silica, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5ce2ad3d85954e69a9b8fd82cb956518
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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