(Diethylamino)sulfur trifluoride → HCID 86638157, compound

HRID 423411Notes

Reaction equation

HRID 423411 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11](O)[CH:10]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:25])CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([F:25])[C@H:10]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 66673794HCID 66673794, compound

Product 1

HCID 86638157HCID 86638157, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve 4′-hydroxy[1,3′]bipyrrolidinyl-1′-carboxylic acid tert-butyl ester (573 mg, 2.24 mmol) in dichloromethane (15 mL) and cool the mixture to −78° C. Add diethylaminosulfur trifluoride (504 mg, 3.13 mmol) dropwise and then allow the mixture to warm to room temperature. Stir the mixture overnight. Evaporate the solution and purify by silica gel chromatography, eluting with 0-3% methanol (2N NH3)/CH2Cl2 to give 520 mg (89%) of the title compound as a yellow oil. 1H NMR(DMSO-d6): δ 1.37 (s, 9H), 1.61-1.67 (m, 4H), 2.43-2.54 (m, 4H), 2.86 (bs, 1H), 3.30-3.41 (m, 1H), 3.45-3.60 (m, 1H), 5.09-5.25 (m, 1H).

Workup

  1. temperatureto warm to room temperature
  2. customEvaporate the solution
  3. custompurify by silica gel chromatography
  4. washeluting with 0-3% methanol (2N NH3)/CH2Cl2

Sources & evidence

ORD record
ord-4ecc7d6a01e946bdbc367b1b8a7788ed
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

Loading…