Reserpine → 6-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-one

HRID 1244028Notes

Reaction equation

HRID 1244028 reaction equation
[C:1]([O-])(=[O:3])C.[NH4+:5].CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)[C:17]2N[C:27]4[CH:32]=[C:31]([O:33]C)[CH:30]=[CH:29][C:28]=4[C:16]=2[CH2:15]C3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O.[C:50](#N)C>>[OH:33][C:31]1[CH:32]=[C:27]2[C:28]([C:16]([CH3:15])([CH3:17])[C:1](=[O:3])[N:5]2[CH3:50])=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 5770ReserpineHCID 6342AcetonitrileHCID 517165Ammonium Acetate

Product 1

HCID 219317776-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-one

Procedure

Under nitrogen, combined 2.05 g of 6-Methoxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (10.0 mmol) with 28 ml of CH2Cl2. Added 22 ml of 1.0 M boron tribromide in CH2Cl2 dropwise over 10 minutes. Stirred at room temperature for 3.5 hours. Poured over ice-H2O and filtered to give 2.32 g of beige solid. 1H NMR (400 MHz, CD3OD) δ 1.25 (6H, s), 3.13 (3H, s), 6.42 (1H, d, J=2.08 Hz), 6.45 (1H, d, J=7.9 Hz), 7.02 (1H, d, J=8.1 Hz). M/z (APCI+) 192.1 (M+1). HPLC (aqueous 200 mM ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 uM, 125×4 mm column) 3.262.

Sources & evidence

ORD record
ord-4ecee4b527d94fc4905ce11a5f02f44e
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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