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

HRID 931324노트

반응식

HRID 931324 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c934e652854d4bc38da1eb8efc767da2
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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