Triphenylphosphine → HCID 67427269, compound

HRID 1667717Notes

Reaction equation

HRID 1667717 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22](O)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:11][C:4]2[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5209483-Fluoro-4-nitrophenolHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 67427269HCID 67427269, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5.0 g (31.80 mmole) of 3-fluoro-4-nitrophenol, 8.32 g (41.31 mmole) of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester and 14.32 g (54.06 mmole) of triphenylphosphine in 100 mL of tetrahydrofuran was added 8.4 mL (54.06 mmole) of diethyl azodicarboxylate. The mixture was stirred at room temperature for 18 hours and then concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexanes (gradient 0:100-40:60) to give 6.94 g of 4-(3-fluoro-4-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (IV.21a).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with ethyl acetate-hexanes (gradient 0:100-40:60)

Sources & evidence

ORD record
ord-52f1d7aded074d43bccc869ca7b7ab9d
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

Loading…