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(S)-(+)-4-(2,3-Epoxypropoxy)carbazole → (S)-4-[2-Hydroxy-3-([4-(4-hydroxyphenoxy)phenyl]-2-methylpropylamino)propoxy]carbazole

HRID 1824336
Notes
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Reaction equation

HRID 1824336 reaction equation
CC(N)(C)C[C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[O:20]1[CH2:22][C@H:21]1[CH2:23][O:24][C:25]1[C:37]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]=2[CH:28]=[CH:27][CH:26]=1>CCO>[OH:20][C@@H:21]([CH2:22][N:30]([C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[CH:16][CH:17]=1)[CH2:29][CH:37]([CH3:25])[CH3:36])[CH2:23][O:24][C:25]1[C:37]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]=2[CH:28]=[CH:27][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazoleHCID 221477954-(4-(2-Methyl-2-aminopropyl)phenoxy)phenol

Product 1

HCID 54318132(S)-4-[2-Hydroxy-3-([4-(4-hydroxyphenoxy)phenyl]-2-methylpropylamino)propoxy]carbazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-(4-(2-Methyl-2-aminopropyl)phenoxy)phenol (0.40 g, 1.55 mmol) was combined with (S)-4-(oxiranylmethoxy)-9H-carbazole (0.250 g, 1.0 mmol) in EtOH (50 mL) and the mixture heated at 60° C. for 20 hours. The mixture was then concentrated in vacuo and the resulting residue chromatographed over silica (1–10% MeOH/CHCl3) which allowed for isolation of the product as the free base. The free base was then dissolved in minimal EtOAc and treated with diethyl ether (25 mL) saturated with HCl. Filtration and drying netted 0.410 g (76%) of product as the HCl salt. MS (FD+): 497. m.p. 80–85° C. (dec). Anal. Calcd for C31H32N2O4.1.3HCl: C, 68.31; H, 6.16; N, 5.14. Found: C, 68.30; H, 6.75; N, 4.62.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe resulting residue chromatographed over silica (1–10% MeOH/CHCl3) which
  3. dissolutionThe free base was then dissolved in minimal EtOAc
  4. additiontreated with diethyl ether (25 mL) saturated with HCl
  5. filtrationFiltration
  6. dry with materialdrying netted 0.410 g (76%) of product as the HCl salt

Sources & evidence

ORD record
ord-bd0f2675f41f4677a083fa61b68f5891
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07041684B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes