Trityl chloride → (s)-2-(Tritylamino)butan-1-ol

HRID 81423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81423
[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 1200842-Amino-1-butanol, (+)-

Produkt 1

HCID 57433108(s)-2-(Tritylamino)butan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-(+)-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 this 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: 33 g (89%). 1H-NMR (d6-DMSO, 250 MHz): δ 0.58 (t, 3H, J=7.26 Hz, —NHCH(CH2CH3)CH2OH), 1.10 (m, 2H, —NHCH(CH2CH3)CH2OH), 2.24 (m, 1H, —NHCH(CH2CH3)CH2OH), 2.39 (m, 1H, —NHCH(CH2CH3)CH2OH), 2.76 & 3.03 (2×m, 2H, —NHCH(CH2CH3)CH2OH), 4.32 (t, 1H, J=4.97 Hz, —NHCH(CH2CH3)CH2OH), 7.15-7.52 (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-dd494d617f7f4aedba107272bac72029
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846696B2

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