Acetic Acid → Benzyl 4-((3-methoxy-3-oxopropyl)amino)piperidine-1-carboxylate

HRID 2366553Notes

Reaction equation

HRID 2366553 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.Cl.[CH3:19][O:20][C:21](=[O:25])[CH2:22][CH2:23][NH2:24].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:19][O:20][C:21](=[O:25])[CH2:22][CH2:23][NH:24][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68419530Benzyl 4-((3-methoxy-3-oxopropyl)amino)piperidine-1-carboxylateYield 87.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of benzyl 4-oxopiperidin-1-carboxylate (10 g), β-alanine methyl ester monohydrochloride (5.99 g), acetic acid (4 mL) and sodium triacetoxyborohydride (10.9 g) in dichloroethane (400 mL) was stirred overnight. The reaction mixture was washed with aqueous saturated sodium bicarbonate solution and saturated saline solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (12.0 g, 87%) as a colorless oil.

Workup

  1. washThe reaction mixture was washed with aqueous saturated sodium bicarbonate solution and saturated saline solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbf878f9950b479389b93ce61546d4ff
Source dataset
uspto-grants-2014_04
Patent number
US08697865B2

Reaction notes

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