HCID 178418573, compound → HCID 178468182, compound

HRID 536323Notes

Reaction equation

HRID 536323 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH:14]=[O:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][Mg]Br>C1COCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH:14]([OH:15])[CH3:17])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 178418573HCID 178418573, compoundHCID 178453955HCID 178453955, compound

Product 1

HCID 178468182HCID 178468182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of (trans)-(4-formyl-cyclohexyl)-carbamic acid tert-butyl ester (4.55 g, 20 mmol) in THF (250 ml) was added methylmagnesium bromide (3M in diethyl ether) (6.67 ml, 20 mmol) during 2 min at −70° C. Stirring was continued for 20 min at −70° C. and then quenched with 1M NH4Cl (200 ml). The mixture was extracted with TBME (2×). The organic phases were washed with brine and dried over Na2SO4, filtered and evaporated to dryness. Purification of the residue by normal phase column chromatography, eluting with EtOAc-heptane 1:1, gave the title compound after crystallization (diisopropyl ether-heptane) as a white solid (1.72 g, 7.0 mmol, 35%). TLC (EtOAc-heptane 1:1) Rf=0.37; 1H NMR (600 MHz, DMSO-d6): 0.86-1.81 (m, 9H), 0.99 (d, 3H), 1.36 (s, 9H), 3.09 (m, 1H), 3.32 (m, 1H), 4.27 (d, 1H), 6.67 (d, 1H)

Workup

  1. customquenched with 1M NH4Cl (200 ml)
  2. extractionThe mixture was extracted with TBME (2×)
  3. washThe organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification of the residue by normal phase column chromatography
  8. washeluting with EtOAc-heptane 1:1

Sources & evidence

ORD record
ord-46bfb976d86c488bb5d4380375ebe384
Source dataset
uspto-grants-2014_10
Patent number
US08859586B2

Reaction notes

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