Pyrrolidine → cis-Tert-butyl 4-methyl-3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate

HRID 931304Notes

Reaction equation

HRID 931304 reaction equation
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[CH2:51][CH2:50][C@H:49]([CH3:52])[C@H:48]([C:53](O)=[O:54])[CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40]>ClCCl>[CH3:52][C@H:49]1[CH2:50][CH2:51][N:46]([C:44]([O:43][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:45])[CH2:47][C@H:48]1[C:53]([N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:54]

Participants

6

Reactant 4

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 86317483(3S,4S)-1-Boc-4-methyl-piperidine-3-carboxylic acid

Product 1

HCID 131735165cis-Tert-butyl 4-methyl-3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HATU) (4.12 g, 10.85 mmol), diisopropylethylamine (2.33 g, 18.08 mmol) and pyrrolidine (782 mg, 10.85 mmol) were added to a solution of cis-1-(tert-butoxycarbonyl)-4-methylpiperidine-3-carboxylic acid (2.2 g, 9.04 mmol) in anhydrous dichloromethane (30 mL) at room temperature. The reaction mixture was stirred at room temperature for 4 h. The mixture was quenched with water and was extracted with dichloromethane. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford cis-tert-butyl 4-methyl-3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate (2.6 g).

Workup

  1. customThe mixture was quenched with water
  2. extractionwas extracted with dichloromethane
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2c9be0abc144677bb4e622def6916f5
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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