(Diethylamino)sulfur trifluoride → HCID 57167112, compound

HRID 2211409Notes

Reaction equation

HRID 2211409 reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]1([C:16]2([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@@H:24]3[C@@H:20]([CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23]3)[C@@:19]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])(O)[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[C:10]1([C:16]2([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@@H:24]3[C@@H:20]([CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23]3)[C@:19]([F:7])([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 22857048HCID 22857048, compound

Product 1

HCID 57167112HCID 57167112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.3 cm3 of diethylaminosulphur trifluoride in 20 cm3 of dry methylene chloride is added dropwise to a solution, cooled to 0° C., of 6.48 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-tert-butoxycarbonyl-perhydroisoindol-4-ol in 70 cm3 of dry methylene chloride. The reaction mixture is stirred at this temperature for 3 hours, washed with 100 cm3 of an aqueous saturated solution of sodium bicarbonate and then with 100 cm3 of an aqueous saturated solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 4.8 cm, height 26 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (95/5 by volume) and collecting fractions of 50 cm3. Fractions 34 to 63 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 2.2 g of (3aS,4S,7aS)-7,7-diphenyl-4-fluoro-4-(2-methoxyphenyl)-2-tert-butoxycarbonyl-perhydroisoindole are obtained in the form of a white foam.

Workup

  1. washwashed with 100 cm3 of an aqueous saturated solution of sodium bicarbonate
  2. dry with materialwith 100 cm3 of an aqueous saturated solution of sodium chloride, dried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 4.8 cm, height 26 cm)
  5. washby eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (95/5 by volume)
  6. customcollecting fractions of 50 cm3
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-40189d14be444b4c851f22079aa6f2eb
Source dataset
uspto-grants-1995_10
Patent number
US05463077

Reaction notes

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