Pyrrolidine → cis-Tert-butyl 2-methyl-5-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate

HRID 931324ノート

反応式

HRID 931324 の反応式
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.[C:39]([O:43][C:44]([N:46]1[C@H:51]([CH3:52])[CH2:50][CH2:49][C@H:48]([C:53](O)=[O:54])[CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40].C[C@H]1NC[C@@H](C(O)=O)CC1>ClCCl.O>[CH3:52][C@H:51]1[CH2:50][CH2:49][C@@H:48]([C:53]([N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)=[O:54])[CH2:47][N:46]1[C:44]([O:43][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:45]

参加物

8

反応物 5

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58504783(3S,6R)-6-Methylpiperidine-3-carboxylic acidHCID 66739888Cis-6-Methyl-Piperidine-1,3-Dicarboxylic Acid 1-Tert-Butyl Ester

生成物 1

HCID 131735166cis-Tert-butyl 2-methyl-5-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HATU) (7.50 g, 19.72 mmol), diisopropylethylamine (7.08 mL, 39.45 mmol) and pyrrolidine (1.40 g, 19.72 mmol) were added to a solution of cis-1-(tert-butoxycarbonyl)-6-methylpiperidine-3-carboxylic acid (synthesized by N-Boc protection of cis-6-methylpiperidine-3-carboxylic acid, analogously prepared by the method described in J. Med. Chem. 2011, 54, 1871-1895.) (4.0 g, 16.44 mmol) in anhydrous dichloromethane (40 mL) at room temperature. The reaction mixture was stirred at room temperature for 4 h. Water was added and the mixture was extracted with dichloromethane. The organics were dried over sodium sulfate and concentrated under reduced pressure to afford cis-tert-butyl 2-methyl-5-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate (4.0 g). The material was used without further purification.

後処理

  1. customanalogously prepared by the method
  2. customat room temperature
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organics were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c934e652854d4bc38da1eb8efc767da2
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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