Triethylamine → Tert-butyl 4-{2-(1-hydroxycyclohexyl)-2-[4-(1-naphthyloxy)phenyl]ethyl}piperazine-1-carboxylate

HRID 28843

Reaktionsgleichung

Reaktionsgleichung von HRID 28843
[OH:1][C:2]1([CH:8]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:30]1(B(O)O)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[OH:1][C:2]1([CH:8]([C:23]2[CH:24]=[CH:25][C:26]([O:29][C:38]3[C:39]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:35]=[CH:36][CH:37]=3)=[CH:27][CH:28]=2)[CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2545321-Naphthaleneboronic acidHCID 68853694Tert-butyl 4-[2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl)ethyl]piperazine-1-carboxylate

Produkt 1

HCID 68854206Tert-butyl 4-{2-(1-hydroxycyclohexyl)-2-[4-(1-naphthyloxy)phenyl]ethyl}piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl 4-[2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl)ethyl]piperazine-1-carboxylate (120 mg, 0.30 mmol), naphthalene-1-boronic acid (54 mg, 0.31 mmol) in dry dichloromethane (2 mL) was added copper(II) acetate (19 mg, 0.10 mmol), triethylamine (71 □L, 0.51 mmol), and powdered 4 Å sieves (100 mg) was stirred at room temperature for 16 h, after which time the reaction was filtered through a pad of Celite®, which was washed with dichloromethane (20 mL), and concentrated in vacuo. The product was purified via Biotage Horizon (FLASH 25 S, silica, gradient from 10% EtOAc/hexane to 60% EtOAc/hexane) to yield tert-butyl 4-{2-(1-hydroxycyclohexyl)-2-[4-(1-naphthyloxy)phenyl]ethyl}piperazine-1-carboxylate as a colorless oil. MS (ESI) m/z 531; HRMS: calcd for C33H42N2O4+H+, 531.32173; found (ESI, [M+H]+), 531.3203.

Aufarbeitung

  1. filtrationafter which time the reaction was filtered through a pad of Celite®, which
  2. washwas washed with dichloromethane (20 mL)
  3. concentrationconcentrated in vacuo
  4. customThe product was purified via Biotage Horizon (FLASH 25 S, silica, gradient from 10% EtOAc/hexane to 60% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e59a8a5faf9e424caf065a566734d401
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419980B2

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