Hydrochloric Acid → (R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride

HRID 931052ノート

反応式

HRID 931052 の反応式
[N:1]1([C:6]([C@@H:8]2[CH2:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:21].O1CCOCC1>ClCCl>[ClH:21].[NH:10]1[CH2:11][CH2:12][CH2:13][C@@H:8]([C:6]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[O:7])[CH2:9]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 28167609(R)-tert-butyl 3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate

生成物 1

HCID 117966306(R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (R)-tert-butyl 3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate (58.82 g, 208.3 mmol) in anhydrous dichloromethane (100 mL) was added hydrogen chloride in 1,4-dioxane (260 mL, 1040 mmol, 4M). The reaction mixture was stirred vigorously at room temperature for 1 h. The solvent was removed under reduced pressure and the residue was left standing overnight at room temperature. The residue was triturated with ether (250 mL). The ether was decanted and dichloromethane was added followed by sonication in a warm bath. The solvent was removed under reduced pressure and the resulting solid was placed under high vacuum at 40° C. for 1 h to afford (R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride (48.41 g). The material was used for the next step without further purification. 1H NMR (400 MHz, CD3OD) δ 1.75-2.05 (m, 8H) 3.04-3.17 (m, 2H) 3.19-3.28 (m, 3H) 3.35-3.66 (m, 4H); MS (ES+) (M+H) 183.3.

後処理

  1. customThe solvent was removed under reduced pressure
  2. waitthe residue was left
  3. waitstanding overnight at room temperature
  4. customThe residue was triturated with ether (250 mL)
  5. customThe ether was decanted
  6. additiondichloromethane was added
  7. customfollowed by sonication in a warm bath
  8. customThe solvent was removed under reduced pressure
  9. waitthe resulting solid was placed under high vacuum at 40° C. for 1 h

出典と根拠

ORDレコード
ord-55864826b1c44afaab221eaf49dd18a7
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

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