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

HRID 20241
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6365
1,1-Dichloroethane
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745623B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes