Piperidine → pyrrolidinyl-N-tert-butylcarbamate

HRID 366307노트

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HRID 366307 반응식
[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

참가 물질

13

반응물 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

생성물 2

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5c825c7c9bfe4311b39db5b57b4e7279
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130180

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