Triethylamine → HCID 58986304, compound

HRID 2217767Notes

Reaction equation

HRID 2217767 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][C@@H:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(N(CC)CC)C>ClCCl.C(#N)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([N:14]2[CH2:18][CH2:17][CH2:16][C@@H:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 6931635H-D-Pro-otbu

Product 1

HCID 58986304HCID 58986304, compoundYield 27.2%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-(trifluoromethyl)phenylboronic acid (190 mg), copper (II) acetate (27 mg) and 4 Å molecular sieves (188 mg) in dichloromethane (4 mL) was stirred at room temperature for 5 min, and (R)-tert-butyl pyrrolidine-2-carboxylate (86 mg) in acetonitrile (0.5 mL) was added followed by triethylamine (0.07 mL). The reaction vial was flushed with oxygen, sealed and stirred at 50° C. for 24 h. The reaction mixture was filtered through a pad of Celite, and the filtrate was evaporated in vacuo. The residue was purified by preparative TLC eluting with 10% ethyl acetate/90% hexanes to give the title compound as a colorless oil (43 mg). HPLC retention time: 1.99 min (method A). MS (ESI) (M+H)+ 316.14. 1H NMR (400 MHz, CDCl3) δ 7.41 (1H, d, J=8.4 Hz), 6.52 (1H, d, J=8.4 Hz), 4.15 (1H, m), 3.53 (1H, m), 3.40 (1H, m), 2.0-2.3 (3H, m), 1.41 (9H, s).

Workup

  1. customThe reaction
  2. customvial was flushed with oxygen
  3. customsealed
  4. stirringstirred at 50° C. for 24 h
  5. filtrationThe reaction mixture was filtered through a pad of Celite
  6. customthe filtrate was evaporated in vacuo
  7. customThe residue was purified by preparative TLC
  8. washeluting with 10% ethyl acetate/90% hexanes

Sources & evidence

ORD record
ord-db8b1843d8234e84ae9447f4f9f33796
Source dataset
uspto-grants-2008_08
Patent number
US07408071B2

Reaction notes

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