Triphenylphosphine → 4-[2-(1-Benzyloxycarbonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 456462Notes

Reaction equation

HRID 456462 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([OH:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2O)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].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>C1COCC1>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:17][CH:13]2[CH2:14][CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:12]2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 561665n-Cbz-3-hydroxypiperidineHCID 11543684Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylate

Product 1

HCID 694231604-[2-(1-Benzyloxycarbonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxy-piperidine-1-carboxylic acid benzyl ester (2.34 g, 8.6 mmol) was dissolved in THF (40 mL) at r.t. 4-(2-Hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (2.4 g, 8.6 mmol) and triphenylphosphine (2.7 g, 10.32 mmol) were added. Diisopropyl azodicarboxylate (2.05 mL, 10.32 mmol) was added dropwise to the solution. The mixture was stirred overnight, and then concentrated under reduced pressure and purified using silica gel chromatography (100% ethyl acetate) to afford the title compound (2.5 g, 55%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified

Sources & evidence

ORD record
ord-358cdf61033d43e3a4f8c14276bf828c
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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