N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamine → HCID 11336441, compound

HRID 507885Notes

Reaction equation

HRID 507885 reaction equation
[C:1]([N:4]1[C@H:8]([CH2:9]O)[C@@H:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[O:6][C:5]1([CH3:22])[CH3:21])(=[O:3])[CH3:2].C(N(CC)C(F)(F)C(F)C(F)(F)[F:29])C>C(Cl)Cl>[C:1]([N:4]1[C@H:8]([CH2:9][F:29])[C@@H:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[O:6][C:5]1([CH3:22])[CH3:21])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 136149N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamineHCID 11186465HCID 11186465, compound2×

Product 1

HCID 11336441HCID 11336441, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

(4R,5R)-3-acetyl-2,2-dimethyl-4-hydroxymethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine (Compound II) (75 g, 0.2291 moles) in methylene chloride (525 ml) reacts with N,N-diethyl-1,1,2,3,3,3-hexafluoro-1-propanamine (Ishikawa Reagent) (76.7 g, 0.3437 moles) at 95-105° C. for about 4 hours. Cooling to 20-25° C., addition to sodium hydroxide (6 g) in water (2500 mL), separation of the methylene chloride layer, distillation and replacement of methylene chloride by isopropanol (750 mL), precipitates the desired product. Filtration, washing with water (100 mL) and isopropanol (75 mL), then drying yields (4S,5R)-3-acetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine (Compound IX: R1 is methylsulfonyl; R2, R3 and R4 are methyl).

Workup

  1. additionaddition
  2. customto sodium hydroxide (6 g) in water (2500 mL), separation of the methylene chloride layer, distillation and replacement of methylene chloride by isopropanol (750 mL)
  3. customprecipitates the desired product
  4. filtrationFiltration
  5. washwashing with water (100 mL) and isopropanol (75 mL)
  6. customdrying

Sources & evidence

ORD record
ord-5aa0627934d04c078d4b1422d3c90e58
Source dataset
uspto-grants-2010_08
Patent number
US07786329B2

Reaction notes

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