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

HRID 2228423Notes

Reaction equation

HRID 2228423 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), triphenylphosphine (7.9 g, 30 mmol) in tetrahydrofuran (100 mL) was added diethyl azodicaroxylate (5.2 g, 30 mmol). The reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added and the solution was washed with saturated NaHCO3 (2×100 mL) and brine (100 mL), dried over Na2SO4, and filtered. The evaporated filtrate was purified by flash chromatography (0-4% ethyl acetate in dichloromethane) giving 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 (bs, 1H), 5.14 (s, 2H), 4.27 (t, J=4.9 Hz, 2H), 3.51 (q, J=5.2 Hz, 2H).

Workup

  1. washthe solution was washed with saturated NaHCO3 (2×100 mL) and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe evaporated filtrate was purified by flash chromatography (0-4% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-4f0529d2fb6a44b49ce13a9e3d6d7689
Source dataset
uspto-grants-2002_07
Patent number
US06417161B1

Reaction notes

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