Sodium Hydroxide → 2-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylcarbamoyl]morpholine-4-carboxylic acid tert-butyl ester

HRID 1401868Notes

Reaction equation

HRID 1401868 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[CH3:35][C:36]1([CH3:55])[CH2:45][CH2:44][C:43]([CH3:47])([CH3:46])[C:42]2[CH:41]=[C:40]([C:48]3[N:53]=[C:52]([NH2:54])[CH:51]=[CH:50][CH:49]=3)[CH:39]=[CH:38][C:37]1=2.[OH-].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14](=[O:16])[NH:54][C:52]2[CH:51]=[CH:50][CH:49]=[C:48]([C:40]3[CH:39]=[CH:38][C:37]4[C:36]([CH3:55])([CH3:35])[CH2:45][CH2:44][C:43]([CH3:47])([CH3:46])[C:42]=4[CH:41]=3)[N:53]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 673240416-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylamine

Product 1

HCID 673232752-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylcarbamoyl]morpholine-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

82 mg (0.36 mmol) of morpholine-2,4-dicarboxylic acid 4-tert-butyl ester and 97 mg (0.39 mmol) of ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) are suspended in 2 ml of THF and stirred at room temperature for 20 min. 100 mg (0.36 mmol) of 6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylamine from step a are added to the mixture. The mixture is stirred further overnight, water is added, the mixture is adjusted to pH 9-10 using a 2N NaOH solution and extracted twice with EA. The combined organic phases are dried, filtered and evaporated (191 mg). The residue is purified by means of flash chromatography on silica gel.

Workup

  1. stirringThe mixture is stirred further overnight
  2. extractionextracted twice with EA
  3. customThe combined organic phases are dried
  4. filtrationfiltered
  5. customevaporated (191 mg)
  6. customThe residue is purified by means of flash chromatography on silica gel

Sources & evidence

ORD record
ord-cecd65411c414631b210db514b9a7695
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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