Triethylamine → HCID 54583892, compound

HRID 2093469Notes

Reaction equation

HRID 2093469 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[N:12]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:17][CH2:16][CH:15]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH2:14][CH2:13]1.C(N(CC)CC)C>ClCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:21]2[CH2:20][CH2:19][CH:18]([CH:15]3[CH2:14][CH2:13][N:12]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:17][CH2:16]3)[CH2:23][CH2:22]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27339594-(Methylthio)phenylboronic acidHCID 117475994,4'-Bipiperidine, 1-boc protected

Product 1

HCID 54583892HCID 54583892, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-methylthiophenylboronic acid (240 mg; 1.43 μmol) in dichloromethane (6 mL) was treated with activated powdered 4 Å molecular sieves (1.5 g), Cu(OAc)2 (87 mg; 0.477 mmol), tert-butyl 4,4′-bipiperidine-1-carboxylate (128 mg; 0.477 mmol) and triethylamine (134 μL; 0.954 mmol). The reaction vessel was purged with oxygen and the mixture stirred under an oxygen atmosphere at ambient temperature for 18 hr. The now brown mixture was filtered through Celite. The eluant was adsorbed onto silica gel. The silica gel was exhaustively eluted without fractionation (1:1 hex/MTBE). The eluant was evaporated to a yellow oil and chromatographed (PTLC; 2:1 hex/MTBE). The major band was collected affording the title compound. LRMS calc: 390.2 obs: 391.1 (M+H), 291.1 (M-BOC+H).

Workup

  1. customThe reaction vessel was purged with oxygen
  2. filtrationThe now brown mixture was filtered through Celite
  3. washThe silica gel was exhaustively eluted without fractionation (1:1 hex/MTBE)
  4. customThe eluant was evaporated to a yellow oil
  5. customchromatographed (PTLC; 2:1 hex/MTBE)
  6. customThe major band was collected

Sources & evidence

ORD record
ord-7af21d029d59491296b1bf7bd23ec0ab
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

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