Triphenylphosphine → HCID 86688411, compound

HRID 75104Notes

Reaction equation

HRID 75104 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)[CH:19]=[CH:20][CH:21]=1.O[CH:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:28]([C:24]1[CH:23]=[C:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH:31]3[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]3)[CH:17]=2)[CH:27]=[CH:26][CH:25]=1)#[N:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 37789923-(3-Hydroxyphenyl)benzonitrile

Product 1

HCID 86688411HCID 86688411, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.210 g (5.99 mmol) of diisopropyl azodicarboxylate is added dropwise to a solution, cooled to 0° C., under an argon atmosphere, of 0.974 g (4.99 mmol) of 3′-hydroxybiphenyl-3-carbonitrile, 1.205 g (5.99 mmol) of tert-butyl 4-hydroxypiperidine-1-carboxylate and 1.570 g (5.99 mmol) of triphenylphosphine in 12 ml of tetrahydrofuran. The mixture is subsequently stirred at ambient temperature overnight. 15 g of silica are added and the mixture is evaporated to dryness. The product is purified by chromatography on silica gel, elution being carried out with a 10:90 and then 15:85 mixture of ethyl acetate and cyclohexane, in order to obtain 1.538 g (4.06 mmol) of product in the form of a colourless oil.

Workup

  1. addition15 g of silica are added
  2. customthe mixture is evaporated to dryness
  3. customThe product is purified by chromatography on silica gel, elution
  4. addition15:85 mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-5ede2699b3aa4e73b4e6c1d1882638ae
Source dataset
uspto-grants-2014_09
Patent number
US08835418B2

Reaction notes

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