Trifluoroacetic acid → 2-Azatricyclo[3.3.1.13,7]dec-5-ylmethanol

HRID 623988Notes

Reaction equation

HRID 623988 reaction equation
[OH:1][CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([N:6]3C(OC(C)(C)C)=O)[CH2:4]1)[CH2:10]2.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:7]12[CH2:12][C:3]3([CH2:2][OH:1])[CH2:10][CH:9]([CH2:11][CH:5]([CH2:4]3)[NH:6]1)[CH2:8]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89720512Tert-butyl 5-(hydroxymethyl)-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate

Product 1

HCID 897149612-Azatricyclo[3.3.1.13,7]dec-5-ylmethanolYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 mL RB flask fitted with magnetic stirrer tert-butyl 5-(hydroxymethyl)-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate, Intermediate-15 (0.12 g, 0.45 mmol) in DCM (5 mL) was added. The reaction mixture was cooled to 00° C. followed by addition of trifluoroacetic acid (0.26 g, 2.2 mmol). This mixture was stirred for 4 hours. After completion of the reaction (reaction was monitored by LCMS) reaction mixture was concentrated followed by trituration with mixture of hexane:ether (1:1) to give Intermediate-16 (0.12 g, yield=97%) as an oily mass.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to 00° C
  3. customAfter completion of the reaction (reaction was monitored by LCMS) reaction mixture
  4. concentrationwas concentrated
  5. additionfollowed by trituration with mixture of hexane:ether (1:1)
  6. customto give Intermediate-16 (0.12 g, yield=97%) as an oily mass

Sources & evidence

ORD record
ord-6c7fcacb72004c15958373698836343f
Source dataset
uspto-grants-2016_04
Patent number
US09303016B2

Reaction notes

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