Triphenylphosphine → HCID 178487968, compound

HRID 2279293Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18](=[O:29])[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][OH:28])[CH2:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14].[CH3:30][O:31][C:32]1[N:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]=[CH:37][C:36](O)=[CH:35]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[C:13]([O:17][C:18](=[O:29])[NH:19][C@H:20]1[CH2:21][CH2:22][C@H:23]([CH2:26][CH2:27][O:28][C:36]2[CH:37]=[N:38][C:39]3[C:34]([CH:35]=2)=[N:33][C:32]([O:31][CH3:30])=[CH:41][CH:40]=3)[CH2:24][CH2:25]1)([CH3:16])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 30 °C

Procedure

Diethyl azodicarboxylate (3.96 g, 22.72 mmol, 3.0 eq) is added at room temperature to a stirred solution of [trans-4-(2-hydroxy-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (1.84 g, 7.57 mmol, 1.0 eq), 6-methoxy-[1,5]naphthyridin-3-ol (1.80 g, 10.22 mmol, 1.35 eq) and triphenylphosphine (5.96 g, 22.72 mmol, 3.0 eq) in tetrahydrofuran (70 mL). After 14 hours stirring at 30° C., tetrahydrofuran is evaporated and the resulting crude product is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 6:1, v/v) to afford {trans-4-[2-(6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as an off-white solid (1.65 g, 53.5% yield).

Workup

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

Sources & evidence

ORD record: ord-b4697c5801a64265a3d3435b39b379eb
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133219B2

Reaction notes

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