Piperidine → pyrrolidinyl-N-tert-butylcarbamate

HRID 366307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366307
[C:1]([NH:5][C:6](=[O:8])[O-:7])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][NH:12]1.C[Si](C)(C)C1CCCN1.CC1C=C(C2CCCCN2)C=CC=1.CC1C=C(C2CCCN2)C=CC=1.N1CCCCC1.N1CCCC1.[H-].[Na+].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[N:12]1([N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6](=[O:7])[O-:8])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:11]1.[N:12]1([N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6](=[O:7])[O-:8])[CH2:13][CH2:14][CH2:15][CH2:16]1

Komponenten

13

Edukt 10

HCID 8082PiperidineHCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 35440982-(3-Methylphenyl)pyrrolidineHCID 44294402-(3-Methylphenyl)piperidineHCID 177527332-TrimethylsilylpyrollidineHCID 21252905Tert-butylcarbamateHCID 232891542-Trimethylsilylpiperidine

Produkt 2

HCID 131722116piperidinyl-N-tert-butylcarbamateAusbeute 89 %HCID 131722117pyrrolidinyl-N-tert-butylcarbamateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

It is necessary to use a protecting group to prepare certain amines. A suitable protecting group is tert-butylcarbamate ("BOC") which was used to prepare 2-trimethylsilylpiperidine, 2-trimethylsilylpyrollidine, 2-(3-methylphenyl)piperidine, and a 2-(3-methylphenyl)pyrrolidine. The BOC group was attached by generating the anion from either piperidine or pyrrolidine using sodium hydride in tetrahydrofuran. This solution was cooled to 5° C. and a slight excess of di-tert-butyldicarbonate added. After two hours, the solution was poured into saturated sodium bicarbonate and the layers separated. The organic layer was dried over magnesium sulfate and the solvent removed by rotary evaporation. Distillation at reduced pressure provided either piperidinyl-N-tert-butylcarbamate (bp 95° C., 3 mm Hg, 89% yield) or pyrrolidinyl-N-tert-butylcarbamate (bp 69° C., 1 mm Hg, 95% yield).

Aufarbeitung

  1. customthe layers separated
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent removed by rotary evaporation
  4. distillationDistillation at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5c825c7c9bfe4311b39db5b57b4e7279
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130180

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