Triethylamine → 3-(3-Pyridyl)-1-propyl (2S)-N-(alpha-toluene-sulfonyl)pyrrolidine-2-carboxylate

HRID 635247Notes

Reaction equation

HRID 635247 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:7].[C:18]1([CH2:24][S:25](Cl)(=[O:27])=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[C:18]1([CH2:24][S:25]([N:1]2[CH2:5][CH2:4][CH2:3][C@H:2]2[C:6]([O:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:7])(=[O:27])=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 154276663-(3-Pyridyl)-1-propyl pyrrolidine-2-carboxylate

Product 1

HCID 154276683-(3-Pyridyl)-1-propyl (2S)-N-(alpha-toluene-sulfonyl)pyrrolidine-2-carboxylateYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(3-Pyridyl)-1-propyl pyrrolidine-2-carboxylate (200 mg; 0.9 mmol) and α-toluenesulfonyl chloride (160 mg; 0.9 mmol) in methylene chloride (20 mL) was treated with triethylamine (90 mg; 0.9 mmol) and stirred for 2 hours at room temperature. The reaction mixture was filtered to remove solids and applied directly to a silica gel column, eluting with 50% ethyl acetate in hexane, to obtain 150 mg (43%) of Compound 4 (Table I) as a clear oil. 1H NMR (300 MHz, CDCl3): δ1.81-1.85 (m, 2H); 1.95-2.02 (m, 3H); 2.10-2.25 (m, 1H); 2.69-2.74 (t, 2H); 2.85-2.97 (m, 1H); 3.24-3.27 (m, 1H); 4.16-4.20 (m, 2H); 4.29 (d, 1H); 4.34 (m, 1H); 4.45 (d, 1H); 7.20-7.25 (m, 1H); 7.35 (m, 3H); 7.49-7.52 (m, 3H); 8.46 (s, 2H). Analysis calculated for C20H24N2O3S: C, 61.83; H, 6.23; N, 7.21. Found: C, 61.59; H, 6.24; N, 7.17.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove solids
  3. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-44bcf083e398406b9a8aac61f99583d7
Source dataset
uspto-grants-2001_02
Patent number
US06187796B1

Reaction notes

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