Sodium Carbonate → (S)-benzyl 3-(ethylamino)piperidine-1-carboxylate

HRID 919580Notes

Reaction equation

HRID 919580 reaction equation
C(O[C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1)=O)(C)(C)C.[C:25]([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[CH2:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1)[CH3:25]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 50999241(S)-1-Cbz-3-Boc-Aminopiperidine

Product 1

HCID 66569232(S)-benzyl 3-(ethylamino)piperidine-1-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate (300 mg, 0.82 mmol) in 1,4-dioxane (2.5 mL) was treated with dioxane. HCl (5 mL) and the solution was stirred at rt 1 h. The solvent was reduced in vacuo to afford a residue which was then dissolved in water (5 mL). The aqueous solution was treated with solid Na2CO3 and the aqueous solution was extracted with EtOAc (3×15 mL). The combined organic layer was dried over Na2SO4, concentrated in vacuo to yield titled intermediate (217 mg, 92%), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 7.36-7.26 (m, 5H), 5.13 (s, 2H), 4.20-3.82 (m, 2H), 2.94-2.60 (m, 5H), 1.94-1.92 (m, 1H), 1.69-1.68 (m, 1H), 1.47-1.28 (m, 3H), 1.09 (t, J=6.8 Hz, 3H). ES-MS: m/z [M+1]=263.

Workup

  1. customto afford a residue which
  2. extractionthe aqueous solution was extracted with EtOAc (3×15 mL)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acba3083b7c34c77877dc2163a395882
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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