tert-butyl 3-formyl-1H-indole-1-carboxylate → HCID 86590908, compound

HRID 985640Notes

Reaction equation

HRID 985640 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=O)=[CH:9]1)=O)(C)(C)C.[BH-](O[C:29]([CH3:31])=[O:30])(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:12]1([CH3:13])[CH:11]=[CH:10][CH:9]=[CH:31][C:29]=1[O:30][C:14]1[CH:15]=[C:16]2[C:11]([CH2:17][CH2:10][CH2:9][NH:8]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2764519tert-butyl 3-formyl-1H-indole-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86590908HCID 86590908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-formyl-indole-1-carboxylic acid t-butyl ester, Compound 9, where R1 is 4-tolyl, R2 is H, R3 is 2-methylprop-1-yl, and R4 is CH3 (9 mg (0.0609 mmol) and NaBH(OAc)3 (17 mg, 0.0812 mmol) in 1 mL of anhydrous CH2Cl2 was vigorously stirred for 2 days, during which the the initially cloudy solution turned clear. The mixture was partitioned between 5 mL of EtOAc and 3 mL of saturated-NH4Cl solution and extracted three times. The combined EtOAc layer was washed with brine, dried over Na2SO4 and evaporated to dryness under vacuum. The product was purified by a silica gel column with Hexane/EtOAc (4/1-2/1) to afford 15 mg of 7-tolyloxy-3,4-dihydro-2H-quinoline-1-(3-methyl-indole-3-yl-1-carboxylic acid t-butyl ester)-4-spiro-5′-3′-1(2-methylpropy-1-yl)-1′ methyl-imidazolidine-2′,4′-dione as a light brown oil (71% yield).

Workup

  1. customThe mixture was partitioned between 5 mL of EtOAc and 3 mL of saturated-NH4Cl solution
  2. extractionextracted three times
  3. washThe combined EtOAc layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness under vacuum
  6. customThe product was purified by a silica gel column with Hexane/EtOAc (4/1-2/1)

Sources & evidence

ORD record
ord-0f14b3bd6ae0400d95099edd324327eb
Source dataset
uspto-grants-2005_03
Patent number
US06872827B2

Reaction notes

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