Acetic Acid → HCID 68419530, compound

HRID 20241

Reaction equation

HRID 20241 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 68419530HCID 68419530, compoundYield 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-de45e883b33e49fb877442f2ee862f0f
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Linked notes

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