Trifluoroacetic acid → 6,7-Difluoro-3,3a,4,8b-tetrahydroindeno[2,1-d]oxazol-2-one

HRID 2060885Notes

Reaction equation

HRID 2060885 reaction equation
C([O:8][C:9](=[O:23])[NH:10][CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][C:15]([F:21])=[C:16]([F:20])[CH:17]=2)[C:12]1=O)C1C=CC=CC=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>>[F:20][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[F:21])[CH:12]1[CH:11]([NH:10][C:9](=[O:8])[O:23]1)[CH2:19]2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59401382(5,6-Difluoro-1-oxoindan-2-yl)carbamic acid benzyl ester

Product 1

HCID 594013946,7-Difluoro-3,3a,4,8b-tetrahydroindeno[2,1-d]oxazol-2-one

Procedure

To (5,6-difluoro-1-oxoindan-2-yl)carbamic acid benzyl ester (Preparation 79) (238 mg, 0.75 mmol) was added TFA (5 mL) and triethylsilane (0.59 mL, 3.75 mmol). The reaction mixture was stirred for 24 h. Solvent was removed in vacuo and the residue purified by column chromatography (MeOH:DCM 5:95) to give the title compound: δH (CDCl3) 3.06-3.15 (1H, m), 3.29 (1H, dd), 4.79 (1H, t), 5.98 (1H, d), 7.10 (1H, dd), 7.27-7.35 (1H, m), 12.02 (1H, s).

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue purified by column chromatography (MeOH:DCM 5:95)

Sources & evidence

ORD record
ord-81621b83403d4ce184fd06d6907d83d5
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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