(Diethylamino)sulfur trifluoride → HCID 69996021, compound

HRID 1359858Notes

Reaction equation

HRID 1359858 reaction equation
CCN(S(F)(F)[F:7])CC.[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[C:22]([N:24]1[CH2:29][CH2:28][CH:27](O)[CH2:26][CH2:25]1)=[O:23])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(Cl)Cl>[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[C:22]([N:24]1[CH2:29][CH2:28][CH:27]([F:7])[CH2:26][CH2:25]1)=[O:23])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 699936691,1-Dimethylethyl (2R)-2-[(4-hydroxy-1-piperidinyl)carbonyl]-1-pyrrolidinecarboxylate

Product 1

HCID 69996021HCID 69996021, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DAST (1.2 mL, 9 mmol) was added to a solution of (R)-2-(4-hydroxy-piperidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (2.6 g, 8.7 mmol) in DCM at −78° C. The mixture was stirred at rt for 20 hours. The reaction was cooled to 0° C., quenched with sodium bicarbonate and extracted with DCM. The organic layer was concentrated and purified on a silica gel column to give 1.5 g of (R)-2-(4-fluoro-piperidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with sodium bicarbonate
  3. extractionextracted with DCM
  4. concentrationThe organic layer was concentrated
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-caced7ea12b1471cbf5e396298b1fe4d
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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