Ammonia → 1-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctylamine

HRID 402547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402547
[Si:1]([O:8][CH:9]1[CH2:16][CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:18].[CH2:19](B1OC(C)(C)C(C)(C)O1)[CH:20]=[CH2:21]>CO>[CH2:19]([C:13]1([NH2:18])[CH2:14][CH2:15][CH2:16][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][CH2:11][CH2:12]1)[CH:20]=[CH2:21]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolaneHCID 109780905-(Tert-butyldimethylsilyloxy)cyclooctanone

Produkt 1

HCID 685558261-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctylamineAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1.5 g (5.85 mmol) of 5-(tert-butyldimethylsilyloxy)cyclooctanone in 8.4 mL (58.5 mmol) of 7N ammonia in methanol, previously stirred for 15 min at room temperature, were added dropwise 1.7 mL (9.36 mmol) of 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane. The reaction mixture was stirred for 18 h at room temperature. The volatiles were removed in vacuo and the residue redissolved in 100 mL of diethyl ether. Then, 100 mL of 1 N aqueous HCl were added dropwise and the resultant biphasic mixture was stirred for 30 min. The layers were separated, the aqueous layer was washed with diethyl ether and the pH adjusted to pH9 by the addition of sodium hydroxide. The suspension was then extracted with a 3:1 mixture of dichloromethane and 2-propanol and the combined organic extracts were concentrated in vacuo to afford 0.89 g of the title compound as mixture of diastereomers. Rt=0.44 min, 0.49 min (Method C). Detected mass: 184.3 (M+H+).

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue redissolved in 100 mL of diethyl ether
  3. additionThen, 100 mL of 1 N aqueous HCl were added dropwise
  4. stirringthe resultant biphasic mixture was stirred for 30 min
  5. customThe layers were separated
  6. washthe aqueous layer was washed with diethyl ether
  7. additionthe pH adjusted to pH9 by the addition of sodium hydroxide
  8. extractionThe suspension was then extracted with a 3:1 mixture of dichloromethane and 2-propanol
  9. concentrationthe combined organic extracts were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-928e4412e1ab472f9a9b1d51f206eb39
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742116B2

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