Acetic Anhydride → HCID 90201151, compound

HRID 718766Notes

Reaction equation

HRID 718766 reaction equation
[CH2:1]([C:3]12[CH2:23][CH2:22][C:17]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:16][CH:4]1[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([CH3:15])=[CH:10][C:9]=12)[CH3:2].[C:24]([O-])(=[O:26])[CH3:25].[K+].C(OC(=O)C)(=O)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([C@:3]12[CH2:23][CH2:22][C:17]3([O:18][CH2:19][CH2:20][O:21]3)[CH2:16][C@H:4]1[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([NH:14][C:24](=[O:26])[CH3:25])[C:11]([CH3:15])=[CH:10][C:9]=12)[CH3:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 86722344HCID 86722344, compound

Product 1

HCID 90201151HCID 90201151, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

rac-(4aR,11bS)-11b-ethyl-10-methyl-1,2,4,4a,5,6,7,11b-octahydrospiro[dibenzo[a,c][7]annulene-3,2′-[1,3]dioxolan]-9-amine (24, R2=Ethyl) (0.178 g, 0.563 mmol) was dissolved in DCM (4 mL) then potassium acetate (0.138 g, 1.408 mmol) and acetic anhydride (0.115 g, 1.126 mmol) were added. After about 10 min sat. aq. NaHCO3 (3 mL) was added and the mixture was diluted with DCM (15 mL). The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified on silica gel (12 g) using a gradient of 0-50% EtOAc in DCM. Product fractions were combined and concentrated under reduced pressure to yield rac-N-((4aR,11bS)-11b-ethyl-10-methyl-1,2,4,4a,5,6,7,11b-octahydrospiro[dibenzo[a,c][7]annulene-3,2′-[1,3]dioxolan]-9-yl)acetamide (25, R2=Ethyl) (0.125 g, 62%); LC/MS, method 3, Rt=2.36 min, MS m/z 358 (M+H)+. 1H NMR (400 MHz, DMSO) δ 9.12 (s, 1H), 7.13 (s, 1H), 6.99 (s, 1H), 3.89-3.73 (m, 4H), 2.87-2.81 (m, 1H), 2.67-2.59 (m, 1H), 2.39-2.32 (m, 1H), 2.22-2.06 (m, 1H), 2.15 (s, 3H) 2.02 (s, 3H), 2.01-1.91 (m, 2H), 1.69-161 (m, 3H), 1.58-1.51 (m, 1H), 1.49-1.20 (m, 5H), 0.61 (t, J=7.5 Hz, 3H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on silica gel (12 g)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0394e10dc8f433aa4e83488c49ccbed
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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