Trifluoroacetic acid → HCID 89720591, compound

HRID 623992Notes

Reaction equation

HRID 623992 reaction equation
[CH:1]1([CH2:4][O:5][C:6]23[CH2:15][CH:10]4[CH2:11][CH:12]([CH2:14][CH:8]([N:9]4C(OC(C)(C)C)=O)[CH2:7]2)[CH2:13]3)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1([CH2:4][O:5][C:6]23[CH2:15][CH:10]4[CH2:11][CH:12]([CH2:14][CH:8]([NH:9]4)[CH2:7]2)[CH2:13]3)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89720588HCID 89720588, compound

Product 1

HCID 89720591HCID 89720591, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged tert-butyl 5-(cyclopropylmethoxy)-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate, Intermediate-19 (50 mg, 0.016 mmol) in DCM (5 mL). Then reaction mixture was cooled to 0° C. and trifluoroacetic acid (0.099 g, 0.084 mmol) was added and stirred for 4 hours. After completion of the reaction (reaction was monitored by LCMS) the reaction mixture was concentrated followed by trituration with mixture of hexane:ether (1:1) to give Intermediate-20 (50 mg, yield=95%) as an oily mass.

Workup

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. customThen reaction mixture
  3. customAfter completion of the reaction (reaction was monitored by LCMS) the reaction mixture
  4. concentrationwas concentrated
  5. additionfollowed by trituration with mixture of hexane:ether (1:1)
  6. customto give Intermediate-20 (50 mg, yield=95%) as an oily mass

Sources & evidence

ORD record
ord-53c872ebcd3040579693ab3ba35c90cd
Source dataset
uspto-grants-2016_04
Patent number
US09303016B2

Reaction notes

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