Acetic Acid → HCID 18679309, compound

HRID 1633453Notes

Reaction equation

HRID 1633453 reaction equation
[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[C:17]([OH:23])[CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][C:25]([CH3:29])=[CH:26][CH:27]=O.C1(B(O)O)C=CC=CC=1.C(O)(=O)C>C1(C)C=CC=CC=1>[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]4[O:23][C:25]([CH3:29])([CH3:24])[CH:26]=[CH:27][C:18]4=3)[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 610203-Methyl-2-butenalHCID 66827Phenylboronic AcidHCID 18679300HCID 18679300, compound

Product 1

HCID 18679309HCID 18679309, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-benzoyl-9-hydroxy-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.306 g, 1.0 mmol), 3-methyl-2-butenal (0.11 mL, 1.1 mmol), phenylboronic acid (0.134 g, 1.1 mmol) and glacial acetic acid (5.0 mL) in anhydrous toluene (37.0 mL) was refluxed for 3 hours under nitrogen in an apparatus fitted with a Dean-Stark trap. After cooling down to room temperature, the mixture was concentrated in vacuo to dryness, the residue was partitioned between water (30.0 mL) and dichloromethane (30.0 mL). The aqueous layer was extracted with dichloromethane (2×30.0 mL). The combined dichloromethane solution was washed with water and NaHCO3 solution successfully, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness and the residue was subjected to column chromatography (EtOAc:hexane, 1:1) to give 0.128 g (34%) of 10-benzoyl-3,3-dimethyl-7,8,9,10,11,12-hexahydro-3H-azepino[4,5-b]pyrano[3,2-e]indole as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.99-7.82, 7.35, 6.94-6.89, 6.76, 6.58, 5.57-5.46, 4.02-3.92, 3.64-3.56, 3.29, 3.05-2.99, 2.78, 1.38, 1.34; MS (ESI+) m/z 373 (M++H).

Workup

  1. temperaturewas refluxed for 3 hours under nitrogen in an apparatus
  2. customfitted with a Dean-Stark trap
  3. concentrationthe mixture was concentrated in vacuo to dryness
  4. customthe residue was partitioned between water (30.0 mL) and dichloromethane (30.0 mL)
  5. extractionThe aqueous layer was extracted with dichloromethane (2×30.0 mL)
  6. washThe combined dichloromethane solution was washed with water and NaHCO3 solution successfully
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-d79266545bb64b26af23e3f95a898748
Source dataset
uspto-grants-2003_01
Patent number
US06503899B2

Reaction notes

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