Triethylamine → tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

HRID 365650Notes

Reaction equation

HRID 365650 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O>C(Cl)Cl>[C:20]([O:19][C:17]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4]1)=[O:16])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5.0 g (43.4 mmol) of 3-hydroxymethyl-piperidine in 200 ml of CH2Cl2, was added 6.05 ml (43.4 mmol) of triethylamine (Et3N), followed by 9.8 ml (43.4 mmol) of (BOC2O). The reaction mixture was stirred for 1 hour at room temperature and then washed with 75 ml of a 0.1N hydrochloric acid solution (HCl), dried over Na2SO4, filtered and then concentrated in vacuo.

Workup

  1. washwashed with 75 ml of a 0.1N hydrochloric acid solution (HCl)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-584fa7b360bf4f15af3fd92551ab3eb0
Source dataset
uspto-grants-2000_10
Patent number
US06127422

Reaction notes

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