N-Hydroxyphthalimide → Benzyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

HRID 1987041Notes

Reaction equation

HRID 1987041 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[CH2:7]([O:6][C:5]([NH:4][CH2:3][CH2:2][O:1][N:16]1[C:17](=[O:26])[C:18]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]2[C:20]1=[O:21])=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 280458benzyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 13983475Benzyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamateYield 91.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl N-(2-hydroxyethyl)carbamate (5.9 g, 30 mmol), N-hydroxyphthalimide (4.9 g, 30 mmol), and triphenylphosphine (7.9 g, 30 mmol) in tetrahydrofuran (100 mL) was added diethyl azodicarboxylate (5.2 g, 30 mmol). The reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added, washed with saturated NaHCO3 (2×100 mL) and brine (100 mL), dried over Na2SO4, and filtered. After evaporating the filtrate, the residue was purified by flash column chromatography (methylene chloride to 4% ethyl acetate in methylene chloride) to give the title compound as a white solid (9.3 g, 91%). 1H-NMR (300 MHz, CDCl3) δ 7.84 (m, 2H), 7.78 (m, 2H), 7.37 (m, 5H), 5.97 (br s, 1H), 5.14 (s, 2H), 4.27 (t, J=4.9 Hz, 2H), 3.51 (q, J=5.2 Hz, 2H).

Workup

  1. washwashed with saturated NaHCO3 (2×100 mL) and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customAfter evaporating the filtrate
  5. customthe residue was purified by flash column chromatography (methylene chloride to 4% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-f4035c4a8f864f0e8a9670e1dcd8775a
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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