HCID 178495875, compound → benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamate

HRID 2068537Notes

Reaction equation

HRID 2068537 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6]1[C@H:12]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][CH2:10][C:9]2[CH:24]=[CH:25][CH:26]=[CH:27][C:8]=2[N:7]=1>C(O)=O>[CH:3]1[N:7]2[C:8]3[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=3[CH2:10][CH2:11][C@@H:12]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]2=[N:5][CH:4]=1

Participants

3

Reactant 1

HCID 178495875HCID 178495875, compound

Product 1

HCID 58304077benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamateYield 85%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve benzyl N-[(3R)-2-(2,2-dimethoxyethylamino)-4,5-dihydro-3H-1-benzazepin-3-yl]carbamate (9.78 g, 24.61 mmol) in formic acid (60 mL, 96%) and heat at 100° C. for 1.5 hours. Allow the mixture to cool and remove the black sediment by filtering it through a glass wool plug. Concentrate the filtrate under reduced pressure, pour it into water, and basify it with 1M NaOH. Add ethyl acetate to the resulting precipitate and separate the organic layer. Extract the aqueous layer with ethyl acetate. Combine, wash (brine), dry over sodium sulfate, and concentrate the organic layers under reduced pressure to give the title compound (6.95 g, 85%): MS (m/z): 334 (M+1), 97.8% ee, Retention time for Isomer 1 (R Isomer), 4.58 min; Isomer 2 (S Isomer), 3.20 min. (Chiralpak AD-H column; 100% EtOH with 0.2% dimethylethylamine; flow rate 1.0 mL/min; 225 nM).

Workup

  1. temperatureAllow the mixture to cool
  2. customremove the black sediment
  3. filtrationby filtering it through a glass wool plug
  4. concentrationConcentrate the filtrate under reduced pressure
  5. additionpour it into water
  6. customAdd ethyl acetate to the resulting precipitate and separate the organic layer
  7. extractionExtract the aqueous layer with ethyl acetate
  8. washCombine, wash (brine)
  9. dry with materialdry over sodium sulfate
  10. concentrationconcentrate the organic layers under reduced pressure

Sources & evidence

ORD record
ord-765a54daec8740af9986d11f37835065
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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