Sulfamide → (S)-3-((4-methoxybenzyl)oxy)pyrrolidine-1-sulfonamide

HRID 1849560Notes

Reaction equation

HRID 1849560 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][O:8][C@H:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:5][CH:4]=1.[S:16](N)([NH2:19])(=[O:18])=[O:17]>C(COC)OC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C@H:9]2[CH2:13][CH2:12][N:11]([S:16]([NH2:19])(=[O:18])=[O:17])[CH2:10]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 86325453(S)-3-((4-methoxybenzyl)oxy)pyrrolidine

Product 1

HCID 86702905(S)-3-((4-methoxybenzyl)oxy)pyrrolidine-1-sulfonamideYield 61.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (S)-3-((4-methoxybenzyl)oxy)pyrrolidine (4.50 g, 21.7 mmol) and sulfamide (2.50 g, 26.0 mmol) in dimethoxyethane (100 mL) was refluxed for 72 h. The reaction was concentrated in vacuo. Purification of the residue by column chromatography (30% to 100% gradient ethyl acetate in hexanes) afforded the title compound as a colorless solid (3.80 g, 61%): 1H NMR (300 MHz, DMSO-d6) δ 7.27-7.24 (m, 2H), 6.91-6.88 (m, 2H), 6.74 (s, 2H), 4.39 (s, 2H), 4.16-4.11 (m, 1H), 3.74 (s, 3H), 3.30-3.25 (m, 1H), 3.18-3.10 (m, 3H), 2.00-1.88 (m, 2H); MS (ES+) m/z 287.2 (M+1); MS (ES−) m/z 285.3 (M−1).

Workup

  1. temperaturewas refluxed for 72 h
  2. concentrationThe reaction was concentrated in vacuo
  3. customPurification of the residue by column chromatography (30% to 100% gradient ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-58351dbfb46a4b508592f691f9cd5ac9
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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