Water → cis-3-(1H-indol-3-yl)-indan-1-ol

HRID 1435771Notes

Reaction equation

HRID 1435771 reaction equation
C[O-].[Na+].[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C@@H:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:15]([O:22]C(=O)CCC)[CH2:14]2)=[CH:5]1.[NH4+].[Cl-].O>CO>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C@@H:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:15]([OH:22])[CH2:14]2)=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 86618890butyric acid (1R,3S)-3-(1H-indol-3-yl)-indan-1-yl ester

Product 1

HCID 68910747cis-3-(1H-indol-3-yl)-indan-1-olYield 89.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3 mL 30% NaOMe in methanol was added to 13.49 g butyric acid (1R,3S)-3-(1H-indol-3-yl)-indan-1-yl ester in 100 mL methanol. TLC showed full conversion after 1.5 hours. 1.5 g solid NH4Cl and 50 mL water were added. Methanol was removed in vacuo and after aqueous work up, (1R,3S)-3-(1H-indol-3-yl)-indan-1-ol (37.9 mmol ) was obtained.

Workup

  1. customafter 1.5 hours
  2. customMethanol was removed in vacuo

Sources & evidence

ORD record
ord-43a20ef6ae0c4929a9655bac2755a109
Source dataset
uspto-grants-2009_11
Patent number
US07618967B2

Reaction notes

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