Diisopropylethylamine → (S)-benzyl 1-(3-nitrophenyl)ethylcarbamate

HRID 735647Notes

Reaction equation

HRID 735647 reaction equation
[C:1](=[O:18])(ON1C(=O)CCC1=O)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[N+:20]([C:23]1[CH:24]=[C:25]([C@@H:29]([NH2:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21].CCN(C(C)C)C(C)C>C(Cl)Cl>[N+:20]([C:23]1[CH:24]=[C:25]([C@@H:29]([NH:31][C:1](=[O:18])[O:2][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:30])[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 11344712(S)-1-(3-nitrophenyl)ethanamine hydrochloride

Product 1

HCID 57842774(S)-benzyl 1-(3-nitrophenyl)ethylcarbamateYield 118.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzyl 2,5-dioxopyrrolidin-1-yl carbonate (1.36 g, 5.5 mmol) was added to a solution of (S)-1-(3-nitrophenyl)ethanamine HCl (1 g, 4.95 mmol) in CH2Cl2 (70 mL) and DIEA (2.2 mL, 12.4 mmol) and the reaction mixture was stirred for 1 h. The mixture was diluted with CH2Cl2 (100 mL), washed with NaHCO3, brine, dried over Na2SO4 and concentrated in vacuo to yield 59A (1.76 g, 99%) as a white solid. MS (ESI) m/z 323.02 (M+Na)+.

Workup

  1. washwashed with NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b13a8ad25ea4da498aeabb3a9daa061
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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