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

HRID 1435770Notes

Reaction equation

HRID 1435770 reaction equation
[BH4-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[CH2:13]2)=[CH:4]1.N1C2C(=CC=CC=2)C=C1[C@@H]1C2C(=CC=CC=2)[C@H](O)C1>CO.C1COCC1>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@@H:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C@H:14]([OH:21])[CH2:13]2)=[CH:4]1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 688950613-(1H-indol-3-yl)-indan-1-oneHCID 68915444Racemic cis-3-indolyl-indan-1-ol

Product 1

HCID 68910747cis-3-(1H-indol-3-yl)-indan-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (6.2 g, 163 mmol, 2 equiv.) was added to 3-(1H-indol-3-yl)-indan-1-one (20 g, 80.9 mmol ) in 200 mL methanol and 100 mL THF at 0° C. The reaction mixture was allowed to warm to room temperature over night. Aqueous work up gave racemic cis-3-indolyl-indan-1-ol (quantitative).

Sources & evidence

ORD record
ord-d2eaee945d534e35b61923ac1d864e4f
Source dataset
uspto-grants-2009_11
Patent number
US07618967B2

Reaction notes

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