tert-butyl N-(2-oxoethyl)carbamate → 1-(1,1-Dimethylethyl) 3-ethyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1,3-piperazinedicarboxylate

HRID 2074865Notes

Reaction equation

HRID 2074865 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][NH:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.[C:19]([NH:26][CH2:27][CH:28]=O)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:23][C:22]([O:21][C:19]([NH:26][CH2:27][CH2:28][N:4]1[CH2:5][CH2:6][N:1]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:2][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:20])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 114026711-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylate

Product 1

HCID 592158481-(1,1-Dimethylethyl) 3-ethyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1,3-piperazinedicarboxylate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of 1-(1,1-dimethylethyl) 3-ethyl 1,3-piperazinedicarboxylate [EP1486498, 2004] (2.023 g, 8.28 mmol) in 10 mL of dichloroethane was added a solution of N-boc-2-aminoacetaldehyde (1.87 g, 12.42 mmol) in 20 mL of dichloroethane. The solution was stirred at room temperature and under nitrogen atmosphere for 30 min. Sodium triacetoxyborohydride (3.32 g, 16.56 mmol) was then added and the reaction kept at room temperature overnight. The product was isolated on a SCX cartridge. 2.492 g.

Workup

  1. waitthe reaction kept at room temperature overnight
  2. customThe product was isolated on a SCX cartridge

Sources & evidence

ORD record
ord-1d16bcca62f84ce99ebf2003918e2397
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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