Sodium Hydroxide → 4-(Methoxymethyl)piperidine

HRID 1282000Notes

Reaction equation

HRID 1282000 reaction equation
ClC1C=C(Cl)C=CC=1CN1C[C@H](C2C=CSC=2)[C@@H](C[N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][OH:23])[CH2:18][CH2:17]2)C1.[OH-].[Na+].[CH3:31]C(OC(OC(OC(C)(C)C)=O)=O)(C)C>C(Cl)Cl>[CH3:31][O:23][CH2:22][CH:19]1[CH2:20][CH2:21][NH:16][CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 102969381-(2,4-Dichlorobenzyl)-3-(S)-(4-(hydroxymethyl)piperidinylmethyl)-4-(S)-(3-thienyl)pyrrolidine

Product 1

HCID 47152834-(Methoxymethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 22.2 g (193 mmol) of 4-hydroxymethylpiperidine (Example 8) in 100 mL of CH2Cl2 and 75 mL of a 15% aqueous solution of NaOH was added a solution of 63 g (289 mmol) of Boc2O in 50 ml of CH2Cl2 over a period of 2 h. After stirring for 30 min, the organic layer of the reaction mixture was washed with 15% aqueous NaOH solution and sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate=19:1, then 4:1) to give the title compound.

Workup

  1. washthe organic layer of the reaction mixture was washed with 15% aqueous NaOH solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (silica, hexanes

Sources & evidence

ORD record
ord-0a5499c93add4388884ac0c0669ced6c
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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