Water → HCID 69413841, compound

HRID 1766403Notes

Reaction equation

HRID 1766403 reaction equation
[F:1][C:2]1[CH:41]=[CH:40][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([CH:13]3[CH:20]4[CH:16]([CH2:17][N:18](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH2:19]4)[CH2:15][CH2:14]3)[CH2:8]2)=[CH:4][CH:3]=1.O>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([CH:13]3[CH:20]4[CH:16]([CH2:17][NH:18][CH2:19]4)[CH2:15][CH2:14]3)[CH2:8]2)=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 962WaterHCID 69411592HCID 69411592, compound

Product 1

HCID 69413841HCID 69413841, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(3aRS,4RS,6aSR)-4-[(3S)-3-(4-fluorobenzyl)piperidin-1-yl]-2-trityloctahydrocyclo-penta[c]pyrrole (500 mg, 918 μmol) was dissolved in trifluoroacetic acid (4 mL) to form a dark orange-yellow solution. Water (5 mL) was added dropwise to form a dense slurry, lighter in color. After 40 minutes, the mixture was concentrated under vacuum. The residue was dissolved in ethyl acetate and extracted with 1.0 N aqueous hydrochloric acid. The aqueous phase was washed with ethyl acetate, and then made strongly basic by the addition of 50% aqueous sodium hydroxide. The resulting mixture was extracted several times with ether, and the combined ether phases were dried over sodium sulfate and concentrated, yielding a gum (263 mg, 95%), which was used without further purification. 1H NMR (300 MHz, CDCl3) δ 7.08 (m, 2H), 6.95 (m, 2H), 3.14 (m, 1H), 3.0-2.6 (m, 4H), 2.6-2.3 (m, 7H), 2.0-1.2 (m, 9H), 0.93 (m, 1H). Mass spec (CH4-CI) m/z 303.2 (M+H+, 100%).

Workup

  1. customto form a dark orange-yellow solution
  2. customto form a dense slurry
  3. concentrationthe mixture was concentrated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. extractionextracted with 1.0 N aqueous hydrochloric acid
  6. washThe aqueous phase was washed with ethyl acetate
  7. additionmade strongly basic by the addition of 50% aqueous sodium hydroxide
  8. extractionThe resulting mixture was extracted several times with ether
  9. dry with materialthe combined ether phases were dried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6ff61da723df461d97952f265968499e
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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