HCID 58192809, compound → HCID 58192778, compound

HRID 2092652Notes

Reaction equation

HRID 2092652 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[C:9]1=[O:18])[CH2:15]2)([CH3:4])([CH3:3])[CH3:2].[Li][CH3:21]>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[C:9]1([OH:18])[CH3:21])[CH2:15]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 58192809HCID 58192809, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 58192778HCID 58192778, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C., to a solution of ketone 20C (500 mg, 1.9 mmol) in 20 mL of THF was added MeLi (1.6 M in ether, 5 mL, 8.0 mmol) dropwise. The mixture was stirred at −78° C. for 30 minutes before it was quenched by 5 mL of NH4Cl aq (Sat'd) solution. The mixture was extracted by DCM (5 mL×3) and the combined DCM layers were dried over Na2SO4. Solvent was remove under vacuum and the residue was purified by silica gel chromatography Hexane:EtOAc 1:1(v/v)) to give the title compounds 20D (410 mg, 77%) as a mixture of equatorial and axial isomers. LC-MS (ESR): m/z=282 (M+H)+.

Workup

  1. customwas quenched by 5 mL of NH4Cl aq (Sat'd) solution
  2. extractionThe mixture was extracted by DCM (5 mL×3)
  3. dry with materialthe combined DCM layers were dried over Na2SO4
  4. customSolvent was remove under vacuum
  5. customthe residue was purified by silica gel chromatography Hexane:EtOAc 1:1(v/v))

Sources & evidence

ORD record
ord-8b520491818f40ea86fa891ffb72d91c
Source dataset
uspto-grants-2013_05
Patent number
US08440720B2

Reaction notes

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