Trifluoroacetic acid → 1-Benzyl-3-(3,4,5-trichloro-phenyl)-3-trifluoromethyl-pyrrolidine

HRID 1508315Notes

Reaction equation

HRID 1508315 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]([F:13])([F:12])[F:11])=[CH2:9])[CH:5]=[C:4]([Cl:14])[C:3]=1[Cl:15].[CH2:16]([N:23]([CH2:29]OC)[CH2:24][Si](C)(C)C)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C(OCC)(=O)C>[CH2:16]([N:23]1[CH2:29][CH2:9][C:8]([C:6]2[CH:5]=[C:4]([Cl:14])[C:3]([Cl:15])=[C:2]([Cl:1])[CH:7]=2)([C:10]([F:13])([F:12])[F:11])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 899946011-Benzyl-3-(3,4,5-trichloro-phenyl)-3-trifluoromethyl-pyrrolidineYield 55.11%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1,2,3-trichloro-5-(1-trifluoromethyl-vinyl)benzene (5 g, 18.21 mmol) in dry DCM (50 mL) was added benzyl-methoxymethyl-trimethylsilanylmethyl-amine (Preparation 29, 18.64 mL, 72.86 mmol). Resulting reaction mixture was cooled to 0° C. and TFA (0.14 mL, 1.825 mmol) was added slowly. Reaction mixture was stirred at room temperature for 5 hours. After complete consumption of starting material, reaction mixture was concentrated in vacuo to afford yellow thick oil, which was dissolved in ethyl acetate (50 mL) and washed with saturated sodium bicarbonate solution (3×50 mL). Organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo to afford crude compound which was purified by column chromatography using 230-400 mesh silica to afford product as oily liquid (4.1 g, 55.11%). 1H-NMR (400 MHz, CDCl3) δ: 2.28-2.32 (m, 1H), 2.53-2.62 (m, 1H), 2.67-2.73 (m, 1H), 2.79-2.84 (m, 1H), 3.05 (s, 2H), 3.61-3.70 (m, 2H), 7.26-7.35 (m, 5H), 7.42 (s, 2H). (m/z): 407.9 (M+H).

Workup

  1. customResulting
  2. customreaction mixture
  3. customReaction mixture
  4. customAfter complete consumption of starting material, reaction mixture
  5. concentrationwas concentrated in vacuo
  6. customto afford yellow thick oil, which
  7. washwashed with saturated sodium bicarbonate solution (3×50 mL)
  8. dry with materialOrganic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto afford crude compound which
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c94a55c0b3644ee3be3d521fb0c21156
Source dataset
uspto-grants-2015_12
Patent number
US09221835B2

Reaction notes

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