Ammonium Chloride → Benzyl 3-(2-amino-1-(6-(3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-1H-indol-3-yl)ethyl)-2-methylphenylcarbamate

HRID 2361312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361312
[Si:1]([O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([CH:23]([C:28]4[C:29]([CH3:45])=[C:30]([NH:34][C:35](=[O:44])[O:36][CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH:31]=[CH:32][CH:33]=4)[CH2:24][N+:25]([O-])=O)=[CH:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl-].[NH4+]>CO.O1CCCC1.[Zn]>[NH2:25][CH2:24][CH:23]([C:28]1[C:29]([CH3:45])=[C:30]([NH:34][C:35](=[O:44])[O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:31]=[CH:32][CH:33]=1)[C:18]1[C:17]2[C:21](=[CH:22][C:14]([N:11]3[CH2:12][CH2:13][CH:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[CH2:10]3)=[CH:15][CH:16]=2)[NH:20][CH:19]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 67994623Benzyl 3-(1-(6-(3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate

Produkt 1

HCID 67994692Benzyl 3-(2-amino-1-(6-(3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-1H-indol-3-yl)ethyl)-2-methylphenylcarbamateAusbeute 102,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of benzyl 3-(1-(6-(3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate (1.0324 g, 1.642 mmol) and ammonium chloride (1.317 g, 24.63 mmol) in methanol (32.8 mL) and tetrahydrofuran (32.8 mL) under nitrogen was added zinc (1.610 g, 24.63 mmol), and the reaction was stirred overnight. The solution was filtered through a pad of CELITE® and rinsed with MeOH and THF. The filtrate was concentrated in vacuo, dissolved in EtOAc (100 mL) and water (40 mL). After separation of the layers, the aqueous layer was extracted with EtOAc (2×100 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated in vacuo to give the desired product (1.007 g, 1.682 mmol, 102% yield) as a dark solid.

Aufarbeitung

  1. filtrationThe solution was filtered through a pad of CELITE®
  2. washrinsed with MeOH and THF
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutiondissolved in EtOAc (100 mL)
  5. customAfter separation of the layers
  6. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5e5295c0c24c4007894ef6f73521ff14
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685969B2

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