Triphenylphosphine → HCID 21036666, compound

HRID 1294819Notes

Reaction equation

HRID 1294819 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH:31](O)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH:31]3[CH2:32][CH2:33][N:28]([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[CH2:29][CH2:30]3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 116877404-(4-Hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 21036666HCID 21036666, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-(4-Hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (3.11 g), 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester (3.51 g), and polymer supported triphenylphosphine (6.25 g; loading: 3 mmol/g) in DCM (100 mL) was treated with di-tert-butylazodicarboxylate (3.78 g). After 24 h, the resulting mixture was filtered, and the filtrate was evaporated. Chromatography of the residue (15–30% ethyl acetate/hexanes) gave the title compound as a white solid (3.20 g).

Workup

  1. filtrationthe resulting mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-e337683974784a50b03548861e879533
Source dataset
uspto-grants-2007_07
Patent number
US07241778B2

Reaction notes

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