4-Methylmorpholine → (S)-1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(3,4-dichlorophenyl)-3-(2-methanesulfonyloxyethyl)pyrrolidine

HRID 343510Notes

Reaction equation

HRID 343510 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[N:30][N:29]=[N:28]2)=[CH:23][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C@@:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)([CH2:12][CH2:13][OH:14])[CH2:8]1)=[O:6].CN1CCOCC1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[N:30][N:29]=[N:28]2)=[CH:23][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C@@:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)([CH2:12][CH2:13][O:14][S:40]([CH3:39])(=[O:42])=[O:41])[CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 53771624(S)-1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

Product 1

HCID 53887278(S)-1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(3,4-dichlorophenyl)-3-(2-methanesulfonyloxyethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Combine (S)-1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine (200 mg, 0.44 mmol) and N-methylmorpholine (0.97 mmol) in toluene (10 mL). Add dropwise, methanesulfonyl chloride (0.066 g, 0.57 mmol). After 12 hours, dilute with toluene (20 mL) and extract with 1M hydrochloric acid solution and 5% sodium bicarbonate solution. Dry the organic layer over MgSO4, filter, and concentrate invacuo to give the title compound.

Workup

  1. additionAdd dropwise
  2. extractionextract with 1M hydrochloric acid solution and 5% sodium bicarbonate solution
  3. dry with materialDry the organic layer over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate invacuo

Sources & evidence

ORD record
ord-da92492a1b3444258ec0bc6f1a31011a
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

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