Water → 6-Allyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 722728Notes

Reaction equation

HRID 722728 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7](OC)[N:6]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:4].[CH2:20]([Si](C)(C)C)[CH:21]=[CH2:22].B(F)(F)F.CCOCC.O>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:22][CH:21]=[CH2:20])[N:6]1[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 69808AllyltrimethylsilaneHCID 670935071-Tert-butyl 2-methyl 6-methoxypiperidine-1,2-dicarboxylate

Product 1

HCID 670930876-Allyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxy-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester, 37, (5.0 g, 18.3 mmol) and allyltrimethylsilane (5.8 mL, 36.6 mmol) in CH2Cl2 (125 mL) at −78° C. is added dropwise boron trifluoride etherate (2.5 mL, 19.7 mmol). After 1 h, the solution is poured into water and extracted with EtOAc. The extracts are washed with brine, dried (MgSO4), and concentrated in vacuo. The resulting residue is used in the next step without purification.

Workup

  1. extractionextracted with EtOAc
  2. washThe extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue is used in the next step without purification

Sources & evidence

ORD record
ord-20ebc3726ad047469049dfaf5bac238b
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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