Methyl iodide → Benzyl ((3R,4R)-4-methyl-5-oxotetrahydrofuran-3-yl)carbamate

HRID 1434523

Reaktionsgleichung

Reaktionsgleichung von HRID 1434523
[CH:1](NC(C)C)(C)C.C([Li])CCC.[O:13]=[C:14]1[O:18][CH2:17][C@H:16]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15]1.CI.[Cl-].[NH4+]>C1COCC1.CCCCCC.C[C@H]1O[C@H]2[C@H](O)[C@@H](O)[C@H](OC3C4C(=CC5OCOC=5C=4)[C@@H](C4C=C(OC)C(O)=C(OC)C=4)[C@@H]4[C@@H]3COC4=O)O[C@@H]2CO1.C1COP(NCCCl)(=O)N(CCCl)C1.[NH2-].[NH2-].Cl[Pt+2]Cl.O>[CH3:1][C@H:15]1[C:14](=[O:13])[O:18][CH2:17][C@@H:16]1[NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

10

Edukt 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 697924(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamateHCID 178418339Butyllithium

Produkt 1

HCID 13108321Benzyl ((3R,4R)-4-methyl-5-oxotetrahydrofuran-3-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 56841950ICE protocol 1KatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

272 μl (1.9 mmol) diisopropylamine are placed in 3 ml THF and while cooling with ice 1.2 ml (1.9 mmol) of an n-butyllithium solution in hexane (1.6M) are added. The mixture is stirred for 10 minutes at 0° C., then cooled to −78° C. and a solution of 200 mg (0.85 mmol) benzyl (R)-(5-oxo-tetrahydrofuran-3-yl)-carbamate in 1 ml THF is added dropwise. The mixture is stirred for one hour at −78° C. Then 210 μl (3.3 mmol) methyl iodide are added dropwise, and the mixture is heated to −60° C. within one hour. Then 0.5 ml sat. ammonium chloride solution is added and the mixture is heated to ambient temperature. Water is added and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated to dryness. The residue is taken up in DMF, acidified with TFA and purified by reversed-phase chromatography.

Aufarbeitung

  1. temperaturecooled to −78° C.
  2. stirringThe mixture is stirred for one hour at −78° C
  3. temperaturethe mixture is heated to −60° C. within one hour
  4. temperaturethe mixture is heated to ambient temperature
  5. extractionthe mixture is extracted three times with ethyl acetate
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. customevaporated to dryness
  8. custompurified by reversed-phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5b312c38ffbe4103ae25f7061656ab9e
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615549B2

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