Benzyl Alcohol → Tert-butyl 5-benzyloxy-3-oxo-azepane-1-carboxylate

HRID 1754289Notes

Reaction equation

HRID 1754289 reaction equation
[O:1]=[C:2]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][CH:4]=[CH:3]1.[CH2:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC([O-])(C)C.[K+].O>[CH2:16]([O:23][CH:4]1[CH2:5][CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C:2](=[O:1])[CH2:3]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 75464896tert-Butyl 3-oxo-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

Product 1

HCID 118222054Tert-butyl 5-benzyloxy-3-oxo-azepane-1-carboxylateYield 183.5%

Reagents, catalysts & solvents 2

HCID 23665647Potassium tert-butoxideCatalystHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of tert-butyl 6-oxo-3,7-dihydro-2H-azepine-1-carboxylate (540.00 mg, 2.56 mmol, 1.00 Eq) in BnOH (2.76 g, 25.56 mmol, 10.00 Eq), was added t-BuOK (28.68 mg, 255.61 umol, 0.10 Eq) in one portion under N2. The mixture was stirred at 20° C. for 12 hours. LCMS showed the reaction was completed. The mixture was poured into water (100 mL) and stirred for 20 min. The aqueous phase was extracted with EA (40 mL*2). The combined organic phase was washed with saturated brine (20 mL*3), dried with anhydrous Na2SO4, filtered and concentrated in vacuum to afford tert-butyl 5-benzyloxy-3-oxo-azepane-1-carboxylate (1.50 g, crude) as yellow oil.

Workup

  1. stirringstirred for 20 min
  2. extractionThe aqueous phase was extracted with EA (40 mL*2)
  3. washThe combined organic phase was washed with saturated brine (20 mL*3)
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-9032d3b27c114f96b9fa49931ccbcb07
Source dataset
uspto-grants-2015_10
Patent number
US09169212B2

Reaction notes

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