Hydrochloric Acid → HCID 178468185, compound

HRID 1036536Notes

Reaction equation

HRID 1036536 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](N(OC)C)=[O:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][Li].Cl>C1COCC1>[CH2:1]([O:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([C:15](=[O:16])[CH3:21])[CH2:13][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 178418348HCID 178418348, compoundHCID 178502735HCID 178502735, compound

Product 1

HCID 178468185HCID 178468185, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

Cis-4-(benzyloxy)-N-methoxy-N-methylcyclohexanecarboxamide (1.3 g, 4.7 mmol) was dissolved in THF (10 mL). CH3Li (3.0 M solution in diethoxymethane, 8.0 mL, 14.1 mmol, 3.0 eq.) was added to the solution dropwise at −70° C. The mixture was stirred at −70° C. under nitrogen atmosphere for 1 h. then 1 M HCl solution was added to the mixture until pH=6. The mixture was extracted with ethyl acetate and the organic layer was concentrated and purified by silica gel column chromatography using petroleum ether/ethyl acetate (3/1) as eluent to give product as a slight yellow oil (720 mg, 60%). 1H NMR (400 MHz, CDCl3) δ 7.34-7.25 (m, 5H), 4.49 (s, 2H), 3.62-3.60 (m, 1H), 2.40-2.25 (m, 1H), 2.13 (s, 3H), 1.97-1.93 (m, 2H), 1.86-1.80 (m, 2H), 1.67-1.54 (m, 2H), 1.53-1.47 (m, 2H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2d6e07513e724e0aa0f99a4adc5684f4
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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