Piperidine → pyrrolidinyl-N-tert-butylcarbamate

HRID 366307ノート

反応式

HRID 366307 の反応式
[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

参加物

13

反応物 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

生成物 2

HCID 131722116piperidinyl-N-tert-butylcarbamate収率 89%HCID 131722117pyrrolidinyl-N-tert-butylcarbamate収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5c825c7c9bfe4311b39db5b57b4e7279
出典データセット
uspto-grants-2000_10
特許番号
US06130180

反応ノート

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