Tetrabutylammonium Fluoride → (3aR, 7R,7aR)-2-t-butoxycarbonyl-4,4-diphenyl-7-fluoroperhydroisoindole

HRID 1721202Notes

Reaction equation

HRID 1721202 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([C@@H:11](OS(C(F)(F)F)(=O)=O)[CH2:12][CH2:13][C:14]2([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-:37].C([N+](CCCC)(CCCC)CCCC)CCC>FCF.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([C@H:11]([F:37])[CH2:12][CH2:13][C:14]2([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57263029(3aR, 7S, 7aR)-2-t-butoxycarbonyl-4,4-diphenyl-7-trifluoromethylsulphonyloxyperhydroisoindole

Product 1

HCID 54399787(3aR, 7R,7aR)-2-t-butoxycarbonyl-4,4-diphenyl-7-fluoroperhydroisoindole

Reagents, catalysts & solvents 2

HCID 6345DifluoromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 4.87 g of (3aR, 7S, 7aR)-2-t-butoxycarbonyl-4,4-diphenyl-7trifluoromethylsulphonyloxyperhydroisoindole in 150 cm3 of dry difluoromethane is treated with 22.6 cm3 of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran and then stirred for 17 hours at 20° C and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.2-0.063 mm, diameter 4.5 cm, height 35 cm), eluting under a nitrogen pressure of 0.4 bar with a cyclohexane and ethyl acetate mixture (75/25) and collecting fractions of 20 cm3. Fractions 28 to 38 are pooled and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.44 g of (3aR, 7R,7aR)-2-t-butoxycarbonyl-4,4-diphenyl-7-fluoroperhydroisoindole in the form of white crystals; melting point 200° C., [α]D20 =-225° C. (c=1, CHCl3).

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  2. customThe residue is chromatographed on a silica gel column (particle size 0.2-0.063 mm, diameter 4.5 cm, height 35 cm)
  3. washeluting under a nitrogen pressure of 0.4 bar with a cyclohexane and ethyl acetate mixture (75/25)
  4. customcollecting fractions of 20 cm3
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-5c2051163a3f4f1290f2a4fb554a5f05
Source dataset
uspto-grants-1996_04
Patent number
US05508433

Reaction notes

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