(Diethylamino)sulfur trifluoride → HCID 69997073, compound

HRID 1359703Notes

Reaction equation

HRID 1359703 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([N:15]1[CH2:19][CH2:18][C@@H:17](O)[CH2:16]1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:27])CC>ClCCl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([N:15]1[CH2:19][CH2:18][C@@H:17]([F:27])[CH2:16]1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86588614HCID 86588614, compound

Product 1

HCID 69997073HCID 69997073, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of S)-2-((R)-3-hydroxy-pyrrolidin-1-ylcarbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.8 g, 2.8 mmol) in dichloromethane (5 mL) at −78° C., was added slowly DAST (0.4 mL, 3 mmol). After stirring at room temperature for 3 h, the reaction mixture was diluted with methanol and concentrated. The residue was dissolved in EtOAc and washed with sodium bicarbonate solution (3×), sodium chloride (1×). After concentrating, the residue was purified to give 700 mg (87%) of (S)-2-((R)-3-fluoro-pyrrolidin-1-ylcarbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with sodium bicarbonate solution (3×), sodium chloride (1×)
  4. concentrationAfter concentrating
  5. customthe residue was purified

Sources & evidence

ORD record
ord-7ddf0e666b774c9abdfc16c0e9bc6458
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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