HCID 58192767, compound → HCID 58192802, compound

HRID 2092643Notes

Reaction equation

HRID 2092643 reaction equation
[O:1]=[C:2]1[CH:9]2[CH2:10][C:5]3([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[Li][CH3:21]>C1COCC1>[C:15]([O:14][C:13](=[O:19])[NH:12][C:5]12[CH2:4][CH:3]3[CH2:11][CH:7]([CH2:8][CH:9]([C:2]3([OH:1])[CH3:21])[CH2:10]1)[CH2:6]2)([CH3:16])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 58192767HCID 58192767, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 58192802HCID 58192802, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C., to a solution of 7B (400 mg, 1.51 mmol) in 5 mL of THF was added MeLi (1.6 M in ether, 2.36 mL, 3.78 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 [0 to 5% of MeOH in DCM:Hexane 1:1(v/v)] to give the title compounds (9A) as a mixture of equatorial and axial isomers (310 mg, 7.3%)). 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 [0 to 5% of MeOH in DCM:Hexane 1:1(v/v)]

Sources & evidence

ORD record
ord-a929f129640c4e199bae5ef717569c44
Source dataset
uspto-grants-2013_05
Patent number
US08440720B2

Reaction notes

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