Methyl chloroformate → HCID 66734972, compound

HRID 1963342Notes

Reaction equation

HRID 1963342 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)[CH2:8][CH:9]1[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][NH:10]1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[C:35](Cl)(=[O:38])[O:36][CH3:37]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)[CH2:8][CH:9]1[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][N:10]1[C:35]([O:36][CH3:37])=[O:38])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731768HCID 66731768, compound

Product 1

HCID 66734972HCID 66734972, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(3,5-di-tert-butylbenzyl)piperidine-4-carboxylate (3.691 g, 10.68 mmol) was dissolved in DCM (80 mL) and DIPEA (2.233 mL, 12.82 mmol) added followed by methyl carbonochloridate (1.262 mL, 16.02 mmol). The solution was stirred at room temperature for 1.5 h. The reaction mixture was washed with 0.1 M HCl and satd NaHCO3. The organic phase was passed through a phase separator and evaporated to yield dimethyl 2-(3,5-di-tert-butylbenzyl)piperidine-1,4-dicarboxylate (3.91 g, 91%) as a yellow oil. MS m/z 404 (M+H)+

Workup

  1. washThe reaction mixture was washed with 0.1 M HCl
  2. customevaporated

Sources & evidence

ORD record
ord-4b637aae977b48058e27e80082cdbafc
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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