Triphenylphosphine → HCID 67427544, compound

HRID 1667722Notes

Reaction equation

HRID 1667722 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]([CH2:25]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.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][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 5209483-Fluoro-4-nitrophenolHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 67427544HCID 67427544, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1.0 g (6.37 mmole) of 3-fluoro-4-nitrophenol, 1.78 g (8.27 mmole) of 4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester, 2.81 g (10.71 mmole) of triphenylphosphine and 50 mL of tetrahydrofuran was added 1.67 mL (10.71 mmole) of diethylazodicarboxylate. 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 2.16 g of 4-(3-fluoro-4-nitro-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (IV.23).

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-5dee8f8c1b26466a8cb41b64c7be4ebb
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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