(Diethylamino)sulfur trifluoride → HCID 131737113, compound

HRID 60767Notes

Reaction equation

HRID 60767 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Si:10]([O:27][CH2:28][C@H:29]1[O:33][C:32](=[O:34])[C@H:31]([C:35](O)([CH3:37])[CH3:36])[CH2:30]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[Si:10]([O:27][CH2:28][C@H:29]1[O:33][C:32](=[O:34])[C@H:31]([C:35]([F:7])([CH3:37])[CH3:36])[CH2:30]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 131737112HCID 131737112, compound2×

Product 1

HCID 131737113HCID 131737113, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of diethylaminosulfur trifluoride (414 μL, 3.0 mmol) in DCM (10 mL) at −78° C. was added a solution of (3S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(1-hydroxy-1-methyl-ethyl)tetrahydrofuran-2-one (compound 40e, 1.03 g, 2.5 mmol) in DCM (10 mL) dropwise. The resulting mixture was warmed up to room temperature and stirred at room temperature overnight. The resulting mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 0-20% EtOAc in petroleum ether) to afford 820 mg of (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(1-fluoro-1-methyl-ethyl)tetrahydrofuran-2-one (compound 40f) as a viscous oil. MS obsd. (ESI+) [(M+H)+]: 415.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel (eluting with 0-20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-503dc65edc444d3494ece39aa441b708
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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