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Triphenylphosphine → {1-[2-(4-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

HRID 1019993
Notes
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Reaction equation

HRID 1019993 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[N:29]=2)[N:24]=[CH:23][C:22]=1[OH:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:34]([O:38][C:39](=[O:50])[NH:40][CH:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48]O)[CH2:43][CH2:42]1)([CH3:37])([CH3:36])[CH3:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CO.C(OCC)(=O)C>[C:34]([O:38][C:39](=[O:50])[NH:40][CH:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][O:33][C:22]2[CH:23]=[N:24][C:25]3[C:30]([C:21]=2[O:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[CH2:43][CH2:42]1)([CH3:37])([CH3:36])[CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 45076484[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl esterHCID 1363794134-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-ol

Product 1

HCID 66746573{1-[2-(4-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester
Yield 116.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl azodicarboxylate (5.48 g, 31.46 mmol, 2.0 eq) is added at room temperature to a stirred solution of 4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-ol (4.44 g, 15.73 mmol, 1.0 eq), [1-(2-hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (5.76 g, 23.59 mmol, 1.5 eq) and triphenylphosphine (8.25 g, 31.46 mmol, 2.0 eq) in tetrahydrofuran (150 mL). After 15 hours stirring at room temperature, tetrahydrofuran is evaporated and the resulting crude product is purified by column chromatography (silica gel, eluent: ethyl acetate:methanol, 10:0 to 9:1, v/v) to afford {1-[2-(4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester as a light brown viscous oil (9.31 g, 88% yield).

Workup

  1. customtetrahydrofuran is evaporated
  2. customthe resulting crude product is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-e8a5248067754cc2bd61f4a17eeabcad
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716280B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes