Sodium Hydroxide → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 380499Notes

Reaction equation

HRID 380499 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[OH-].[Na+].[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O>C(Cl)Cl>[C:15]([O:14][C:12]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4][CH2:5]1)=[O:11])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 4207714-Piperidinemethanol

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 22.2 g (193 mmol) of 4-hydroxymethylpiperidine in 100 mL of CH2Cl2 and 75 mL of a 15% solution of NaOH was added a solution of 63.2 g (289 mmol) of BOC2O in 50 mL of CH2Cl2 over 2 h. After stirring for a further 30 min, the reaction mixture was extracted with 15% NaOH solution and sat'd Nacl solution. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ehtyl acetate, 19:1, then 4:1, then 1:1) to give 25 g of the title compound.

Workup

  1. extractionthe reaction mixture was extracted with 15% NaOH solution
  2. dry with materialThe organic fraction was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (silica, hexanes

Sources & evidence

ORD record
ord-6ac731cdee574b60a3477c1d25b4a1de
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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