Trifluoroacetic acid → HCID 67284671, compound

HRID 1618758Notes

Reaction equation

HRID 1618758 reaction equation
[N:1]1([C:7]2[CH:12]=[C:11]3[N:13](C(OC(C)(C)C)=O)[CH2:14][C:15]4([CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]4)[C:10]3=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1([C:7]2[CH:12]=[C:11]3[NH:13][CH2:14][C:15]4([CH2:20][CH2:19][S:18](=[O:21])(=[O:22])[CH2:17][CH2:16]4)[C:10]3=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67284857HCID 67284857, compound

Product 1

HCID 67284671HCID 67284671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 6-(4-morpholinyl)-2′,3′,5′,6′-tetrahydrospiro-[indole-3,4′-thiopyran]-1(2H)-carboxylate 1′,1′-dioxide (60 mg, 0.142 mmol) in DCM (1 mL) was added TFA (438 μL, 5.68 mmol) and the reaction was stirred at rt for 1 h. After this time the reaction was evaporated in vacuo and dried on the vacuum pump overnight. The resulting residue was then partitioned between DCM (40 mL) and NaHCO3 (10 mL, sat. aqueous solution). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo to give 6-morpholin-4-yl-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran]1′,1′-dioxide. Mass Spectrum (ESI) m/e=323.2 (M+1).

Workup

  1. customAfter this time the reaction was evaporated in vacuo
  2. customdried on the vacuum
  3. waitpump overnight
  4. customThe resulting residue was then partitioned between DCM (40 mL) and NaHCO3 (10 mL, sat. aqueous solution)
  5. dry with materialThe separated organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2f951acd539c49b9ad548664fa20e171
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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