Methyl 5-[2-(benzyloxy)phenyl]-6-cyclohexyl-3-formyl-4-(methoxymethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate → methyl 6-cyclohexyl-5-(2-hydroxyphenyl)-4-(methoxymethyl)-3-methyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008996Notes

Reaction equation

HRID 1008996 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:19]([CH2:20][O:21][CH3:22])[C:18]2[C:23]([CH:30]=O)=[C:24]([C:26]([O:28][CH3:29])=[O:27])[S:25][C:17]=2[C:16]=1[CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)C1C=CC=CC=1>CCOC(C)=O>[CH:32]1([C:16]2[C:17]3[S:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[C:23]([CH3:30])[C:18]=3[N:19]([CH2:20][O:21][CH3:22])[C:15]=2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

3

Reactant 1

HCID 86629785Methyl 5-[2-(benzyloxy)phenyl]-6-cyclohexyl-3-formyl-4-(methoxymethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 67298636methyl 6-cyclohexyl-5-(2-hydroxyphenyl)-4-(methoxymethyl)-3-methyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 5-[2-(benzyloxy)phenyl]-6-cyclohexyl-3-formyl-4-(methoxymethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate was dissolved in EtOAc and the solution was degassed. Pd/C was added and after degassing again hydrogen atmosphere (60 psi) was applied. After hydrogenating for 2 days the catalyst was filtered off and all volatiles were evaporated i. vac. An off-white solid was obtained (89%). MS (ES+) m/z 414 (M+H)+.

Workup

  1. customthe solution was degassed
  2. additionPd/C was added
  3. customafter degassing again hydrogen atmosphere (60 psi)
  4. filtrationthe catalyst was filtered off
  5. customall volatiles were evaporated i
  6. customAn off-white solid was obtained (89%)

Sources & evidence

ORD record
ord-a33333c8b73c4c668935da7a651d9fec
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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