Trityl chloride → (2R)-2-[(Triphenylmethyl)amino]butan-1-ol

HRID 1984259

Reaktionsgleichung

Reaktionsgleichung von HRID 1984259
[NH2:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].CCN(C(C)C)C(C)C.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCC>C(Cl)Cl.CO.CCOCC>[C:16]([NH:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

8

Edukt 4

HCID 6456Trityl chlorideHCID 8058HexaneHCID 81531DiisopropylethylamineHCID 27238562-Amino-1-butanol, (-)-

Produkt 1

HCID 57395035(2R)-2-[(Triphenylmethyl)amino]butan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of (R)-(−)-2-aminobutan-1-ol (10 g, 1 eq, 112.18 mmol) in DCM (500 mL) under an argon atmosphere at room temperature, was added DIEA (30 mL, 1.54 eq, 172.22 mmol) followed by trityl chloride. (35.4 mL, 1.13 eq, 126.98 mmol). The reaction mixture was stirred at room temperature for 48 h, when TLC (hexane:ether:MeOH; 55:40:5) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue precipitated from acetone (50 mL) with hexane (900 mL) with stirring, the precipitate was removed by filtration and the filtrate was evaporated in vacuo. The residue was dissolved in hexane (1 L), filtered, and the filtrate was evaporated in vacuo to afford the title compound as a light yellow oil. Yield: 32 g (86%). 1H-NMR (d6-DMSO, 250 MHz): δ 0.56 (t, 3H, J=7.41 Hz, —NHCH(CH2CH3)CH2OH), 1.10 (m, 2H, —NHCH(CH2CH3)CH2OH), 2.22 (m, 1H, —NHCH(CH2CH3)CH2OH), 2.38 (m, 1H, —NHCH(CH2CH3)CH2OH), 2.72+3.00 (2×m 2H, —NHCH(CH2CH3)CH2OH), 4.28 (t, 1H, J=5.26 Hz, —NHCH(CH2CH3) CH2 OH), 7.14-7.49 (m, 15H, 3×Ph).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue precipitated from acetone (50 mL) with hexane (900 mL)
  3. stirringwith stirring
  4. customthe precipitate was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. dissolutionThe residue was dissolved in hexane (1 L)
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4a6e37b863034a6daca49f488f4ca38a
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544689B2

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