Ethyl Acetoacetate → HCID 59376005, compound

HRID 661487Notes

Reaction equation

HRID 661487 reaction equation
N1C2CCCC(=O)C=2C=C1.C(OCC)(=O)CC(C)=O.P([O-])(O)(O)=O.[Na+].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:40][C:41]1[NH:42][C:43]2[C:44](=[O:55])[CH2:45][CH2:46][CH2:47][C:48]=2[C:49]=1[C:50]([O:52]CC)=[O:51]>>[CH3:40][C:41]1[NH:42][C:43]2[C:44](=[O:55])[CH2:45][CH2:46][CH2:47][C:48]=2[C:49]=1[C:50]([OH:52])=[O:51]

Participants

6

Reactant 5

HCID 8868Ethyl AcetoacetateHCID 14812Phosphorus oxide (P4O10)HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 23672064Monosodium phosphateHCID 59376018ethyl 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate

Product 1

HCID 59376005HCID 59376005, compound

Procedure

In one more aspect, the present invention relates to pyrrolo[b]cyclohexanone, the intermediate of Formula (II), which is synthesized by the route outlined below: 6-amino-5-oxohexanoic acid hydrochloride(S1) and ethyl acetoacetate were refluxed in a.q. sodium dihydrogen phosphate to generate substituted pyrrole(S2). Then the compound S2 was solved in polyphosphoric acid (PPA), P2O5 used as dehydrant, reacted to generate ethyl 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate (S3) at 70° C. 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (S4) is obtained by the hydrolysis of (S3) in 1 mol/L a.q. LiOH. Finally, S4 is reacted with H—R6 at room temperature for 24 hours in DMF to give pyrrolo[b]cyclohexanone of Formula (II) by using a condensation reagent.

Workup

  1. temperaturewere refluxed in a.q
  2. customreacted
  3. customat 70° C

Sources & evidence

ORD record
ord-30cdfd34733a40c6b35131191a3d4dc2
Source dataset
uspto-grants-2011_12
Patent number
US08084621B2

Reaction notes

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