HCID 23003909, compound → HCID 23003927, compound

HRID 396719Notes

Reaction equation

HRID 396719 reaction equation
C([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17](CC(OC)=O)[CH:18]([C:23]([O:25][CH3:26])=[O:24])[C:19](OC)=O)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)(OC(C)(C)C)=O>Cl>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH:18]([CH2:19][CH2:18][C:23]([O:25][CH3:26])=[O:24])[C:23]([O:25][CH3:26])=[O:24])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 23003909HCID 23003909, compound

Product 1

HCID 23003927HCID 23003927, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of dimethyl 3-(1-boc-2,3-dihydro-1H-indol-5-yl)-2-methoxycarbonyl-pentanedioate [530 mg, Reference Example 10(a)] and concentrated hydrochloric acid (20 ml) was stirred at reflux overnight then evaporated. The residual clear foam (370 mg) was treated with methanol (20 ml), then with concentrated sulphuric acid (10 drops). The resulting solution was stirred at reflux for 2 hours then evaporated. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer and extracts were washed with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petrol (1:1, v/v) to give the title compound (150 mg) as a clear oil. MS (ES+) 278 (MH+).

Workup

  1. temperatureat reflux overnight
  2. customthen evaporated
  3. additionThe residual clear foam (370 mg) was treated with methanol (20 ml)
  4. stirringThe resulting solution was stirred
  5. temperatureat reflux for 2 hours
  6. customthen evaporated
  7. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with ethyl acetate
  10. washThe combined organic layer and extracts were washed with brine
  11. customdried
  12. customevaporated
  13. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petrol (1:1

Sources & evidence

ORD record
ord-e1e26b9a5f2646d49abfb51180e5272f
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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