Thiomorpholine 1,1-dioxide → HCID 59756032, compound

HRID 1360341Notes

Reaction equation

HRID 1360341 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:24]=[S:25]1(=[O:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>O1CCOCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)(=[O:15])=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:28]2[CH2:29][CH2:30][S:25](=[O:31])(=[O:24])[CH2:26][CH2:27]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6484228Thiomorpholine 1,1-dioxideHCID 10382042(S)-1-Benzyl-3-[(P-tolylsulfonyl)oxy]pyrrolidine

Product 2

HCID 10382042(S)-1-Benzyl-3-[(P-tolylsulfonyl)oxy]pyrrolidineHCID 59756032HCID 59756032, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

(S)-Toluene-4-sulfonic acid 1-benzyl-pyrrolidin-3-yl ester was prepared as described in J. Med. Chem. 1992, 35, 4205. (S)-Toluene-4-sulfonic acid 1-benzyl-pyrrolidin-3-yl ester (400 mg, 1.208 mmol, 1 eq) and 1,1-dioxo-thiomorpholine (817 mg, 6.042 mmol, 5 eq) were taken up in dioxane and heated at 140° C. for 20 hours. The reaction mixture was cooled and the dioxane was removed using rotary evaporation. The resulting residue was purified on a Biotage 40M amine column using a gradient of 0-50% ethyl acetate/hexanes to obtain the title compound (88 mg, 25%) as a yellow oil. 1H NMR (400 MHz) CDCl3 δ 7.30-7.20 (m, 5H), 3.55-3.54 (s, 2H), 3.19-3.17 (m, 1H), 3.01-2.91 (m, 6H), 2.62-2.58 (m, 2H), 2.51-2.43 (m, 2H), 2.00-1.97 (m, 2H), 1.71-1.67 (m, 2H). ESMS m/z: 295.2 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe dioxane was removed
  3. customevaporation
  4. customThe resulting residue was purified on a Biotage 40M amine column

Sources & evidence

ORD record
ord-90fd67388b3d4c7498000fa447012b15
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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