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Diethyl Ether → [4-(2-Methoxy-pyridin-3-yl)-4-oxo-butyl]-carbamic acid tert-butyl ester

HRID 352136
Notes
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Reaction equation

HRID 352136 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(NC(C)C)(C)C.C[Li].COCN[C:22](=O)[CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].C[CH2:35][O:36]CC>O1CCCC1>[CH3:31][C:28]([O:27][C:26](=[O:32])[NH:25][CH2:24][CH2:23][CH2:22][C:35]([C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:36])([CH3:29])[CH3:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 7912DiisopropylamineHCID 742012-MethoxypyridineHCID 86584230[2-(Methoxymethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl esterHCID 178418348HCID 178418348, compound

Product 1

HCID 102539314[4-(2-Methoxy-pyridin-3-yl)-4-oxo-butyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Methoxypyridine (1.9 ml) and then diisopropylamine (0.1 ml) were added to a solution of methyl lithium (10 ml of a 1.6M solution in ether) in tetrahydrofuran (20 ml) at −78° C. and the solution was stirred at 0° C. for 18hand then re-cooled to −78° C. A solution of 1,1-dimethylethyl [3-(methoxymethylamino)-3-oxopropyl]-carbamate (1.6 g) in tetrahydrofuran (5 ml) was added slowly and the resultant solution was allowed to warm to −30° C. over 3.5 h, quenched with aqueous ammonium chloride and extracted with ether (three times). The combined organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluting with petrol-ether gave the sub-title compound as a colourless oil (0.572 g).

Workup

  1. temperaturethen re-cooled to −78° C
  2. temperatureto warm to −30° C. over 3.5 h
  3. customquenched with aqueous ammonium chloride
  4. extractionextracted with ether (three times)
  5. dry with materialThe combined organic extracts were dried (sodium sulphate)
  6. customevaporated
  7. custompurified by chromatography on silica eluting with petrol-ether

Sources & evidence

ORD record
ord-3e38315d28f442a38cbf626afe239183
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06743939B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes