Hydrochloric Acid → (S)-benzyl 2-oxo-1,4'-bipiperidin-3-ylcarbamate hydrochloride

HRID 407930Notes

Reaction equation

HRID 407930 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([CH:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)[C:13]1=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)[Cl:33].Cl.O1CCOCC1>CO>[ClH:33].[O:31]=[C:13]1[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16][CH2:15][N:14]1[CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 58787267(S)-tert-butyl 3-(benzyloxycarbonylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylate

Product 1

HCID 86688092(S)-benzyl 2-oxo-1,4'-bipiperidin-3-ylcarbamate hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask was charged with (S)-tert-butyl 3-(benzyloxycarbonylamino)-2-oxo-1,4′-bipiperidine-1′-carboxylate (Example 39, Steps A-B; 5.0 g, 12 mmol), CH2Cl2 (50 mL), and methanol (5 mL), 4N HCl in dioxane (29 mL, 116 mmol) was added and the reaction stirred overnight. The reaction was concentrated to afford crude (S)-benzyl 2-oxo-1,4′-bipiperidin-3-ylcarbamate hydrochloride (4.3 g, 100%) which was taken forward without further purification.

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-73d57c7784e0414f9a9b25b1b228621f
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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