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

HRID 1422828Notes

Reaction equation

HRID 1422828 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]

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 esterYield 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-10012b73e45c4c178d73b2a3cda753d8
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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