Sodium borohydride → (1S,3S)-6-chloro-3-phenylindan-1-ol

HRID 1047105Notes

Reaction equation

HRID 1047105 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@H:6]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][C@@H:8]2[OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11997855(S)-6-chloro-3-phenylindan-1-one

Product 1

HCID 11521607(1S,3S)-6-chloro-3-phenylindan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-6-chloro-3-phenylindan-1-one (IVa) can by reduced with sodium borohydride adapting a method described in Bøgesø J. Med. Chem. 1983, 26, 935, using ethanol as solvent and performing the reaction at approximately 0° C., giving compound (Va).

Workup

  1. customthe reaction at approximately 0° C.
  2. customgiving compound (Va)

Sources & evidence

ORD record
ord-0145b28b11784be9959ff0effa40ca49
Source dataset
uspto-grants-2013_10
Patent number
US08569499B2

Reaction notes

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