Tetrahydrofuran → 2-Tosyl-2,3,3a,4-tetrahydrocyclopenta[c]pyrrol-5(1H)-one

HRID 393396Notes

Reaction equation

HRID 393396 reaction equation
[CH2:1]([N:4]([CH2:15][C:16]#[CH:17])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].C1C[O:21][CH2:20]C1>>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([S:5]([N:4]2[CH2:1][CH:2]3[CH2:3][C:20](=[O:21])[CH:17]=[C:16]3[CH2:15]2)(=[O:7])=[O:6])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 7099150Benzenesulfonamide, 4-methyl-N-2-propenyl-N-2-propynyl-

Product 1

HCID 98385022-Tosyl-2,3,3a,4-tetrahydrocyclopenta[c]pyrrol-5(1H)-oneYield 33%

Conditions

Temperature
65 °C

Procedure

To a suspension of the catalyst A precursor resin, shown above {24 mg, 0.025 mmol[Co2(CO)m]} in anhydrous THF(5 cm3) was added N-(2-propenyl)-N-(2-propynyl)-4-methylphenylsulfonamide (125 mg, 0.5 mmol) and the resulting mixture was heated to 65° C. under an atmosphere of CO (50 mbar). After 48 h the mixture was filtered, the resin was washed with THF (2×1 cm3) and the combined filtrates were concentrated in vacuo. 1H-NMR spectroscopy of the pale yellow residue indicated a 1:1 mixture of starting material and product and no by-products. Purification by flash chromatography (SiO2, 20% EtOAc/hexane) gave the title compound (46 mg, 0.167 mmol, 33%) as a white solid; mp 147-149° C.; vmax(CH2Cl2)/cm−1 3058, 1716, 1651, 1350, 1164, 1094, 673; δH (360 MHz)(CDCl3) 1.96-2.02 (1 H, m), 2.32 (3 H, s, CH3), 2.48-2.58 (2 H, m), 3.01-3.36 (1 H, m), 3.93-3.98 (2 H, m), 4.27 (1 H, d, J 16.5), 5.92 (1 H, s, C═CH), 7.28 (2 H, d, J 8, Ar-H), 7.66 (2 H, d, J 8, Ar-H); δC{1H} (90 MHz)(CDCl3) 21.6 (CH3), 39.8 (CH2), 44.0 (CH), 47.7 (CH2), 52.5 (CH2), 126.2 (CH), 127.5 (CH), 130.1 (CH), 133.7 (C), 144.2 (C), 178.6 (C), 207.2 (C═O).

Workup

  1. filtrationAfter 48 h the mixture was filtered
  2. washthe resin was washed with THF (2×1 cm3)
  3. concentrationthe combined filtrates were concentrated in vacuo
  4. additiona 1:1 mixture of starting material and product
  5. customPurification by flash chromatography (SiO2, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-734e62927be74ca8b076612759785d6d
Source dataset
uspto-grants-2004_10
Patent number
US06806389B1

Reaction notes

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