Trifluoroacetic acid → HCID 66590906, compound

HRID 2363500Notes

Reaction equation

HRID 2363500 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.FC(F)(F)C(O)=O.CO[CH2:16][N:17]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)[CH2:18][Si](C)(C)C>ClCCl>[F:31][C:30]([F:32])([F:33])[C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][N:17]1[CH2:18][CH:2]2[C:1](=[O:6])[CH2:5][CH2:4][CH:3]2[CH2:16]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 135882-Cyclopenten-1-oneHCID 66590530HCID 66590530, compound

Product 1

HCID 66590906HCID 66590906, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclopent-2-enone (3.31 g, 40.4 mmol) and trifluoroacetic acid (0.031 mL, 0.404 mmol) were combined in dichloromethane (40 mL). 1-Methoxy-N-(3-(trifluoromethyl)benzyl)-N-((trimethylsilyl)methyl)methanamine (12.33 g, 40.4 mmol) from Step B was added as a solution in 10 mL of dichloromethane dropwise via addition funnel over 45 minutes at room temperature under nitrogen. The reaction was quenched with aqueous sodium bicarbonate and extracted with 2×100 mL of dichloromethane. The organic washes were combined and washed with brine. The solvent was removed in vacuo to give 2-(3-(trifluoromethyl)benzyl)hexahydrocyclopenta[c]pyrrol-4(5H)-one: 1H NMR (300 MHz, CDCl3) δ ppm 7.54-7.34 (m, 4H), 3.66 (d, J=13.4, 1H), 3.52 (d, J=13.4, 1H), 3.04 (dd, J=1.8, 8.9, 1H), 2.91 (ddd, J=2.8, 7.4, 11.7, 1H), 2.72-2.65 (m, 1H), 2.62 (d, J=8.9, 1H), 2.52-2.23 (m, 4H), 2.15 (ddd, J=8.1, 12.9, 17.1, 1H), 1.85-1.70 (m, 1H).

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. extractionextracted with 2×100 mL of dichloromethane
  3. washwashed with brine
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4b4c2d8669df4e05bcb82f67e2e2a819
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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