Sodium Bicarbonate → 1-Benzyl-3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine

HRID 1711393Notes

Reaction equation

HRID 1711393 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:24][S:25]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26].CC(C)([O-])C.[K+].C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[C:18]([CH2:24][S:25]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)(=[O:26])=[O:27])[CH:19]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 23665647Potassium tert-butoxideHCID 588286261-Benzyl-3-(4-nitro-phenoxy)-pyrrolidine

Product 1

HCID 588286161-Benzyl-3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidineYield 47.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-3-(4-nitro-phenoxy)-pyrrolidine (7.2 g, 24 mmol) and 1-chloromethanesulfonyl-naphthalene (5.8 g, 24 mmol) in THF was chilled in an ice bath, treated dropwise with 1.0 M potassium tert-butoxide in THF (55 mL, 55 mmol), stirred at ambient temperatures for 1 hour, 10 minutes, under nitrogen, poured into water, treated with solid sodium bicarbonate and extracted with ethyl acetate. The extracts were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography using 40-60% ethyl acetate in hexane to give 1-benzyl-3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine as a brown gum/foam, 5.7 g (47.1% yield), Mass spectrum (+EI, [M+H]+) m/z 503. 1HNMR (500 MHz, DMSO-d6): δ8.44-8.46 (m, 1H), 8.27 (d, 1H, J=8.30 Hz), 8.07-8.09 (m, 1H), 7.92-7.96 (m, 2H), 7.58-7.66 (m, 3H), 7.19-7.31 (m, 5H), 6.99 (dd, 1H, J=9.15 Hz and 2.81 Hz), 6.66 (d, 1H, J=2.81 Hz), 5.24 (d, 2H, J=2.20 Hz), 4.65-4.69 (m, 1H), 3.53 (s, 2H), 2.59-2.66 (m, 2H), 2.41-2.42 (m, 1H), 2.27-2.34 (m, 1H), 2.00-2.10 (m, 1H), 1.43-1.54 ppm (m, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by flash chromatography

Sources & evidence

ORD record
ord-de0ec44cd16143d7b2bf2de8f7f47d64
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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