(S)-4-bromo-7-fluoro-2,3-dihydro-1H-inden-1-ol → (S)-4-bromo-1-hydroxy-indan-5-carbonitrile
Reaction equation
[Br:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13].BrC1C=CC(F)=C2C=1CC[C@@H]2O>CCCCCC.C(O)C>[Br:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C@@H:6]2[OH:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The compound is synthesized from 4-bromo-1-oxo-indan-5-carbonitrile (2.20 g, 5.1 mmol) in analogy to the preparation of intermediate 2 (Yield 1.30 g). GC (METHOD 1): tR=11.59 min; Mass spectrum (EI+): m/z=237 [M]+, e.e. 98% by chiral HPLC (Column: Daicel Chiralpak OJ-H, 4.6×250 mm, 5 μm Mobile phase: hexane:ethanol 95:5, 1 mL/min, 25° C.) tR=37.52 min.
Sources & evidence
- ORD record
- ord-bde882da123349b4883a5dc8ad3974f1
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09308194B2
Reaction notes
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