Hydrogen chloride-ethyl acetate → Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate

HRID 43478

Reaction equation

HRID 43478 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C@H:13]1[O:25][CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>CO>[CH3:26][O:25][C@H: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][NH:15][CH2:14]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86648489tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

Product 1

HCID 86648490Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl cis(±)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate obtained in Example (40a) (4.28 g, 11.7 mmol) was dissolved in methanol (20 mL). A 4 N hydrochloric acid/ethyl acetate solution (60 mL) was added, and the mixture was stirred at room temperature for 40 minutes. The reaction solution was concentrated under reduced pressure and then saturated aqueous sodium bicarbonate solution was added, followed by extraction with THF. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionsaturated aqueous sodium bicarbonate solution was added
  3. extractionfollowed by extraction with THF
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-c180fdccb7534d8fabcb7c4c30439f79
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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