Methyl iodide → 1-Benzyl 4-methyl 4-((tert-butoxycarbonyl)amino)piperidine-1,4-dicarboxylate

HRID 712292Notes

Reaction equation

HRID 712292 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([O-])([O-])=O.[Cs+].[Cs+].CI>C(#N)C>[C:24]([O:23][C:21]([NH:20][C:14]1([C:17]([O:19][CH3:28])=[O:18])[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12][CH2:13]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 231027164-n-Boc-amino-1-cbz-isonipecotic acid

Product 1

HCID 145370781-Benzyl 4-methyl 4-((tert-butoxycarbonyl)amino)piperidine-1,4-dicarboxylateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an ice-cold solution of 1-((benzyloxy)carbonyl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylic acid (0.50 g, 1.32 mmol) in ACN (15 mL) was added Cs2CO3 (0.52 g, 1.59 mmol) and the resulting reaction mixture stirred at the same temperature for 10 min followed by addition of MeI (0.4 mL, 4.2 mmol). The reaction mixture was stirred for 1 h at rt. After completion of reaction (by TLC), the mixture was passed through celite and solvent was evaporated under reduced pressure to obtain a white solid compound (0.52 g, 96% yield). MS: 393.31 [M+H]+.

Workup

  1. customthe resulting reaction mixture
  2. stirringThe reaction mixture was stirred for 1 h at rt
  3. customAfter completion of reaction (by TLC)
  4. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-68bcc572b2fc458e81d5b8dd82b5c15f
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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