Triphenylphosphine → 4-[2-(1-tert-Butoxycarbonyl-piperidin-4-yloxy)-phenyl]-piperazine-1-carboxylic acid benzyl ester

HRID 456440Notes

Reaction equation

N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:15]([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[OH:37])[CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:38]([O:42][C:43]([N:45]1[CH2:50][CH2:49][CH:48](O)[CH2:47][CH2:46]1)=[O:44])([CH3:41])([CH3:40])[CH3:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:15]([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:37][CH:48]2[CH2:49][CH2:50][N:45]([C:43]([O:42][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:44])[CH2:46][CH2:47]2)[CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Diisopropyl azodicarboxylate (0.70 mL, 3.55 mmol) was added dropwise to a stirred solution of 4-(2-hydroxy-phenyl)-piperazine-1-carboxylic acid benzyl ester (0.74 g, 2.4 mmol), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.48 g, 2.4 mmol) and triphenylphosphine (0.93 g, 3.6 mmol) in THF (25 mL) cooled to 0° C. The resulting solution was warmed to r.t. and stirred for about 16 hours. The solvent was removed in vacuo and the residue purified by silica gel chromatography (20% ethyl acetate in hexanes) to afford the final compound (0.50 g, 43%) as a clear oil.

Workup

temperatureThe resulting solution was warmed to r.t.
customThe solvent was removed in vacuo
customthe residue purified by silica gel chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-7694cb1063474f6aaee8bbc0c429e757
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186715B2

Reaction notes

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