Triethylamine → (2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl ester

HRID 63583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63583
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][NH:11][CH2:12][CH2:13][OH:14])[CH:3]=[CH:2]1.C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>ClCCCl>[CH2:26]([O:25][C:23](=[O:24])[N:11]([CH2:12][CH2:13][OH:14])[CH2:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 219500502-[(1H-Indol-7-ylmethyl)amino]-ethan-1-ol

Produkt 1

HCID 67017088(2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl esterAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-[(1H-indol-7-ylmethyl)-amino]-ethanol (4.4 g) in 1,2-dichloroethane (40 mL) was added triethylamine (4.85 mL, 34.6 mmol) followed by benzyl chloroformate (3.57 mL, 25.34 mmol). The mixture was allowed to stir at room temperature for 2 hours. The mixture was quenched by addition of water (20 mL), and 1.0 M sodium hydroxide (10 mL). The organic layer was separated and the aqueous layer extracted with 1,2-dichloroethane (20 mL). The combined organic extracts were washed with 1.0 M hydrochloric acid (20 mL), water (20 mL), dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography, eluting with 20% ethyl acetate in hexanes to 40% ethyl acetate in hexanes to afford (2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl ester (2.79 g, 52% combined yield for two steps) as a colorless oil. 1H NMR (CDCl3) 400 MHz δ: 9.97 (br s, 1H), 7.75-6.9 (m, 8H), 6.54 (br s, 1H), 5.21 (s, 2H), 4.9-4.6 (m, 3H), 3.85-3.57 (m, 2H), 3.55-3.23 (m, 3H); LCMS M+H=325.

Aufarbeitung

  1. customThe mixture was quenched by addition of water (20 mL), and 1.0 M sodium hydroxide (10 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with 1,2-dichloroethane (20 mL)
  4. washThe combined organic extracts were washed with 1.0 M hydrochloric acid (20 mL), water (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 20% ethyl acetate in hexanes to 40% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-255f3a2f071145a6bba5196e6637abd9
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447088B2

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