Dimethyl Sulfide → HCID 58246966, Verbindung

HRID 1254342

Reaktionsgleichung

Reaktionsgleichung von HRID 1254342
[CH:1]1(Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(C)C.[Si:10]([O:17][CH2:18][CH:19]1[CH2:21][N@@:20]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>C1COCC1.CCOCC>[CH:1]1([CH2:21][C@H:19]([NH:20][C:22](=[O:23])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][O:17][Si:10]([C:13]([CH3:15])([CH3:16])[CH3:14])([CH3:12])[CH3:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 1068Dimethyl SulfideHCID 8728BromocyclopentaneHCID 72525716(S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

Produkt 1

HCID 58246966HCID 58246966, VerbindungAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A 100 mL, three-neck flask was charged with Mg powder (720 mg, 30 mmol), and a solution of cyclopentylbromide (3.73 g, 25 mmol) in THF (25 mL) was added dropwise while the flask was heated with a heat gun. After stirring for about 2 h, most of the Mg had been consumed. The Grignard reagent was added to a suspension of CuBr.SMe2 (307.5 mg, 1.5 mmol) in THF (80 mL) at −78° C., the cuprate was stirred for 30 min and a solution of (S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate (2.87 g, 10 mmol) in ether (30 mL) was added. The mixture was stirred for 2 h, washed with sat'd aq NaHCO3 (2×20 mL) and brine (30 mL), dried over MgSO4, and evaporated. The residue was purified by silica chromatography to obtain tert-butyl (S)-3-cyclopentyl-1-(t-butyldimethylsilyloxy)propan-2-ylcarbamate (2.9 g, 81%) as an oil. 1H NMR (CDCl3, 400 MHZ) δ 0.04 (s, 6 H), 0.89 (s, 9 H), 1.10 (m, 2 H), 1.44 (s, 9 H), 1.50 (m, 3 H), 1.60 (m, 3 H), 1.81 (m, 3 H), 3.58 (m, 3 H), 4.60 (brs, 1 H).

Aufarbeitung

  1. temperaturewas heated with a heat gun
  2. customhad been consumed
  3. additionThe Grignard reagent was added to a suspension of CuBr
  4. washwashed with sat'd aq NaHCO3 (2×20 mL) and brine (30 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5934473a49d44191880642334ebd8b9b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455521B2

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