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

HRID 2168466Notes

Reaction equation

HRID 2168466 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) and washed with ammonium chloride (25 mL) and 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) and brine (25 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washSilica gel chromatography (Reveleris 80 g) eluting
  10. customover 30 minutes

Sources & evidence

ORD record
ord-18eef609322b4b2abca499aecf25c510
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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