Pyridine → HCID 86600825, compound

HRID 1948943Notes

Reaction equation

HRID 1948943 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].[OH:14][C@@H:15]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]1.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][C@@H:15]([O:14][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])[CH2:16]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 1049PyridineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86600825HCID 86600825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-nitrobenzenesulfonyl chloride (4.44 g) in methylene chloride (50 ml) was added to a stirred solution of tert-butyl 3-(R)-hydroxypyrrolidine-1-carboxylate (3.75 g) and pyridine (2.5 ml) in methylene chloride (30 ml) at 10° C. and the mixture allowed to warm to ambient temperature with stirring. The reaction mixture was poured into saturated sodium bicarbonate solution. The organic layer was separated, washed with brine and dried over sodium sulfate. The solution was evaporated under vacuum to give tert-butyl3-(R)-[(4-nitrophenyl)sulfonyloxy]pyrrolidine-1-carboxylate as a yellow crystalline solid. (4.37 g, 59%); 1H NMR Spectrum: (CDCl3) 1.43 (s, 9H), 1.80-2.40 (m, 2H), 3.30-3.65 (m, 4H), 5.20 (hs, 1H), 8.10 (d, 2H), 8.42 (d, 2H).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solution was evaporated under vacuum

Sources & evidence

ORD record
ord-887e2f579b2d4b31920596dffcccce94
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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