tert-Butyl [(4-oxocyclohexyl)methyl]carbamate → HCID 86647903, compound

HRID 2168150Notes

Reaction equation

HRID 2168150 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][CH2:3]1.[CH3:17][Mg]Br>O1CCCC1>[OH:1][C:2]1([CH3:17])[CH2:3][CH2:4][CH:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 40424027tert-Butyl [(4-oxocyclohexyl)methyl]carbamateHCID 178418573HCID 178418573, compound

Product 1

HCID 86647903HCID 86647903, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of tert-butyl (4-oxocyclohexyl)methylcarbamate (1.00 g) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. Methylmagnesium bromide (4.40 mL) was added dropwise. The reaction was stirred for 2 hours at −78° C. then allowed to warm to 0° C. and stirred for 30 minutes. The resulting suspension was quenched with water (10 mL), diluted with ether (50 mL), washed with ammonium chloride (25 mL), washed with brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 80 g) eluting using a gradient of 5% to 50% ethyl acetate/dichloromethane over 30 minutes (flow=60 mL/min) gave the title compound as a 2:1 mixture of cis and trans isomers.

Workup

  1. temperatureto warm to 0° C.
  2. stirringstirred for 30 minutes
  3. customThe resulting suspension was quenched with water (10 mL)
  4. additiondiluted with ether (50 mL)
  5. washwashed with ammonium chloride (25 mL)
  6. washwashed with brine (25 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washSilica gel chromatography (Reveleris 80 g) eluting
  11. customover 30 minutes

Sources & evidence

ORD record
ord-f4111c6c566b42fc8d4b69b7887e72e4
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

Loading…