Trifluoroacetic acid → HCID 22058310, compound

HRID 917111Notes

Reaction equation

HRID 917111 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([OH:14])[CH:10]([OH:22])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.FC(F)(F)C([O-])=O.C(N(CC)CC)C>C(Cl)Cl.O1CCCC1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:11]2([OH:14])[CH2:12][CH2:13][NH:8][CH2:9][CH:10]2[OH:22])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 84468TrifluoroacetateHCID 20812236HCID 20812236, compound

Product 1

HCID 22058310HCID 22058310, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The product of step 2 (500 mg, 1.37 mmol) was dissolved in methylene chloride (10 mL) and the resulting solution cooled to 0° C. Trifluoroacetic acid (3 mL) was slowly added and the reaction was allowed to stir at 0° C. for 2 h, before concentration under reduced pressure. The trifluoroacetate salt was dissolved in tetrahydrofuran and excess triethylamine was added. Solids generated were removed by suction filtration and the supernatant solution was concentrated to afford 4-(4-chloro-phenyl)-piperidine-3,4-diol.

Workup

  1. customSolids generated were removed by suction filtration
  2. concentrationthe supernatant solution was concentrated

Sources & evidence

ORD record
ord-f2acdfb5b28d4c8f8b09a8caf0264d59
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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