Ammonium Chloride → (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(Amino)-2-(3-furanyl)-dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

HRID 12324Notes

Reaction equation

HRID 12324 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:18][C@H:17]([N:19]=[N+]=[N-])[C:16](=[O:22])[C@H:15]2[C@@:6]1([CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@:14]2([CH3:23])[CH2:13][C@@H:12]([C:24]2[CH:28]=[CH:27][O:26][CH:25]=2)[O:11][C:10]1=[O:29])=[O:4].[NH4+].[Cl-]>C(Cl)Cl.CO.[Zn]>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:18][C@H:17]([NH2:19])[C:16](=[O:22])[C@H:15]2[C@@:6]1([CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@:14]2([CH3:23])[CH2:13][C@@H:12]([C:24]2[CH:28]=[CH:27][O:26][CH:25]=2)[O:11][C:10]1=[O:29])=[O:4]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 11531750(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(Azido)-2-(3-furanyl)-dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

Product 1

HCID 44415859(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(Amino)-2-(3-furanyl)-dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 38 (0.08 g, 0.19 mmol), Zn dust (0.16 g, 2.45 mmol) and NH4Cl (g, mmol) in a mixture of CH2Cl2/MeOH (1:4, 20 mL) was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. 2N NaOH (30 mL) was added to the residue and the mixture was extracted with CH2Cl2 (2×20 mL). The combined CH2Cl2 portion was washed with H2O (30 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure afforded 0.06 g (84%) of 39 as a white solid, mp 237-240° C. (EtOAc/n-hexanes.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. addition2N NaOH (30 mL) was added to the residue
  4. extractionthe mixture was extracted with CH2Cl2 (2×20 mL)
  5. washThe combined CH2Cl2 portion was washed with H2O (30 mL)
  6. dry with materialdried (Na2SO4)
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-c717980336e8416f8ee2af5881c025b5
Source dataset
uspto-grants-2010_06
Patent number
US07728001B2

Reaction notes

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