Pyridine → HCID 60036699, compound

HRID 1948922Notes

Reaction equation

HRID 1948922 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14]([O:18][C:19]([N:21]1[CH2:25][C@H:24]([OH:26])[CH2:23][C@H:22]1[C:27](=[O:31])[N:28]([CH3:30])[CH3:29])=[O:20])([CH3:17])([CH3:16])[CH3:15].N1C=CC=CC=1>C(Cl)Cl>[C:14]([O:18][C:19]([N:21]1[CH2:25][C@H:24]([O:26][S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:11])=[O:12])[CH2:23][C@H:22]1[C:27](=[O:31])[N:28]([CH3:29])[CH3:30])=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 25180889(2S,4R)-tert-butyl 2-(dimethylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 60036699HCID 60036699, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

4-Nitrobenzenesulfonyl chloride (0.895 g) was added to a stirred solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2-(N,N-dimethylcarbamoyl)pyrrolidine (0.993 g) and pyridine (0.6 g) in methylene chloride (10 ml) and stirred at 4° C. for 16 hours under an atmosphere of nitrogen. The reaction mixture was washed with aqueous citric acid (1.0 M), saturated sodium bicarbonate and dried over magnesium sulfate. The product was then purified by column chromatography on silica eluting with increasingly polar mixtures of methylene chloride/methanol (100/0 to 95/5). The fractions containing the required product were combined and evaporated under vacuum to give (2S,4R)-1-(tert-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-[(4-nitrophenyl)sulfonyloxy]pyrrolidine as a yellow gum (0.685 g); 1H NMR Spectrum: (DMSO d6) 1.30-1.36 (s, 9H), 1.98-2.07 (m, 1H); 2.37-2.48 (m, 1H); 2.83 (s, 3H), 3.00 (s, 3H), 3.45-3.55 (m, 2H), 4.70 (m, 1H), 5.23 (m, 1H), 8.21 (d, 2H), 8.47 (d, 2H).

Workup

  1. washThe reaction mixture was washed with aqueous citric acid (1.0 M), saturated sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. customThe product was then purified by column chromatography on silica eluting
  4. temperaturewith increasingly polar mixtures of methylene chloride/methanol (100/0 to 95/5)
  5. additionThe fractions containing the required product
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-d338c593503449af9f8e61a53bbb0c4f
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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