Triphenylphosphine → Methyl 3-((2-(N-t-Butyloxycarbonyl-N-methylamino)ethoxy))benzoate

HRID 1598813Notes

Reaction equation

HRID 1598813 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]([O:16][C:17]([N:19]([CH3:23])[CH2:20][CH2:21]O)=[O:18])([CH3:15])([CH3:14])[CH3:13].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:12]([O:16][C:17]([N:19]([CH2:20][CH2:21][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:23])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 88068Methyl 3-HydroxybenzoateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 18930729Methyl 3-((2-(N-t-Butyloxycarbonyl-N-methylamino)ethoxy))benzoateYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-hydroxybenzoate (6.4 g, 42 mmol), alcohol 121a (7.4 g, 42 mmol), diisopropyl azodicarboxylate (8.3 mL, 42 mmol), and triphenylphosphine (11.1 g, 42 mmol) were stirred in dry THF (120 mL) at 0° C. for 1 h, then for 18 h at room temperature. After evaporation of solvent, the product was isolated by chromatography on silica gel, eluting with 0% to 30% EtOAc in hexane to yield a clear oil (9.4 g). IR(film) cm-1 1726, 1696. 1H NMR(300 MHz, CDCl3): 7.64-7.09 (m, 4H), 4.13 (m, 2H), 3.92 (s, 3H), 3.62 (br, 2H), 2.99 (s, 3H), 1.46 (s, 9H). Anal. Cald'd for C16H23NO5 : C, 62.11; H, 7.51; N, 4.53; Found: C, 61.67; H, 7.43; N, 4.47. HR-MS: Calc'd. 310.1654, Found 310. 1650.

Workup

  1. customAfter evaporation of solvent
  2. customthe product was isolated by chromatography on silica gel
  3. washeluting with 0% to 30% EtOAc in hexane

Sources & evidence

ORD record
ord-182c2ae24b424dc9a8453b3c352f73cd
Source dataset
uspto-grants-1998_04
Patent number
US05739163

Reaction notes

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