Water → HCID 59556157, compound

HRID 1809909Notes

Reaction equation

HRID 1809909 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][C:12](=[O:15])[O:13][CH3:14].[CH2:16]1[O:26][C:19]2([CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)[O:18][CH2:17]1.O>C1COCC1.CCOC(C)=O>[OH:25][C:22]1([C:10]2[S:6][C:7]([NH:11][C:12](=[O:15])[O:13][CH3:14])=[N:8][CH:9]=2)[CH2:23][CH2:24][C:19]2([O:18][CH2:17][CH2:16][O:26]2)[CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 962WaterHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 686488HCID 686488, compoundHCID 178418339Butyllithium

Product 1

HCID 59556157HCID 59556157, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of n-butyllithium (10.0 mL of 1.6 M solution in hexane, 15.93 mmol) was added to methyl 1,3-thiazol-2-ylcarbamate (1.05 g, 6.64 mmol) in THF (10 mL) at −78° C. with stirring under N2. After being stirred at −78° C. for 1 h, a solution of 1,4-cyclohexanedione mono-ethylene ketal (1.84 g, 11.75 mmol) in THF (10 mL) was added to the lithiated compound solution via syringe at −78° C. The reaction mixture was allowed to warm to room temperature slowly and stirred overnight. water and EtOAc were added. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with saturated NaCl, dried (MgSO4), concentrated and flash chromatographed (50% EtOAc/hexane to 75% EtOAc/hexane) to give 0.744 g of the title compound in 51% yield. MS (EI) calcd: (M+H)+=315.1. Found: 315.0.

Workup

  1. stirringAfter being stirred at −78° C. for 1 h
  2. stirringstirred overnight
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with saturated NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customflash chromatographed (50% EtOAc/hexane to 75% EtOAc/hexane)

Sources & evidence

ORD record
ord-92aa2107729d4c708c62a810ab79bf0b
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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