Triphenylphosphine → HCID 69411804, compound

HRID 1295579Notes

Reaction equation

HRID 1295579 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])=[O:4].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27](O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([O:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[C:8]([N+:14]([O-:16])=[O:15])[CH:9]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 179651324-(Methoxycarbonylmethoxy)-3-nitrophenol

Product 1

HCID 69411804HCID 69411804, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 4-(methoxycarbonylmethoxy)-3-nitrophenol (6.0 g, 26.8 mmol), 1-(tert-butyloxycarbonyl)-4-hydroxypiperidine (13.8 g, 68.9 mmol) and triphenylphosphine (18.0 g, 68.9 mmol) in tetrahydrofuran (80 mL) at 20° C. under argon was added diisopropyl azodicarboxylate (13.9 g, 68.9 mmol), dropwise over 0.75 h. The resulting solution was stirred at 20° C. for 4 h, then evaporated in vacuo. Chromatography of the residue on silica (400 g) eluting with 5–50% ether in hexane gave the title compound (10.1 g, 93%) as a yellow oil.

Workup

  1. customevaporated in vacuo
  2. washChromatography of the residue on silica (400 g) eluting with 5–50% ether in hexane

Sources & evidence

ORD record
ord-b91f25e5740144f783427141af14795b
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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