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

HRID 707057Notes

Reaction equation

HRID 707057 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][Mg]Br>O1CCCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][C:12]([OH:15])([CH3:17])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

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-9895707da33945b2a94b35b15629b01c
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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