Triphenylphosphine → HCID 66879382, compound

HRID 1796211Notes

Reaction equation

HRID 1796211 reaction equation
[C@@H:1]12[N:8]([CH3:9])[C@@H:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([OH:10])[CH2:2]2.[Cl:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl.O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:10][CH:3]1[CH2:2][C@H:1]2[N:8]([CH3:9])[C@H:5]([CH2:6][CH2:7]2)[CH2:4]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 12074NitrofunginHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 449293120-29-6

Product 1

HCID 66879382HCID 66879382, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-tropanol (6.7 g), 2-chloro-4-nitrophenol (8.2 g) and triphenylphosphine (16.1 g) in a mixture of dichloromethane (200 ml) and tetrahydrofuran (50 ml), diethyl azodicarboxylate (9.7 ml) was added dropwise with stirring under ice-cooling, and the resulting mixture was stirred at room temperature overnight and then evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and methanol (19:1) as the eluent to afford the title compound (8.5 g, yield: 60%) as a pale yellow amorphous solid.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. customevaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-e9288ff1dcb2408ba64043ef1c5d3808
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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