Sulfuric Acid → (1R,2S)-(+)-cis-1-Amino-2-indanol
Reaction equation
[O:1]1[C@@H:3]2[CH2:4][C:5]3[C:10]([C@H:2]12)=[CH:9][CH:8]=[CH:7][CH:6]=3.C(#[N:13])C.S(=O)(=O)(O)O>O>[NH2:13][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1[OH:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -16 °C
Procedure
Into a 300 ml four-neck flask, 10.0 g (75.8 mmol) of cis-(±)-1,2-epoxyindan (VI) and 40 ml of acetonitrile were introduced. This mixture was cooled to -16° C. in an ice/salt bath. To this mixture, 10.62 g (113.6 mmol) of fuming sulfuric acid (containing 25% of sulfuric anhydride) was dropwise added at -13° to -17° C. in a period of 1.5 hour. The mixture was left for 1.5 hour to return to room temperature. An HPLC analysis of the contents revealed that 21.2% of cis-oxazoline derivative (IV: R=CH3) had been generated while no trans-amide derivative (III': R=CH3, Y=OH) was detected. Then, 72 ml of water was added thereto. The resulting mixture was treated in the same manner as Example 8 to yield 5.62 g (yield: 49.8%) of cis-(±)-1-aminoindan-2-ol (V) as a white crystal. Its purity determined by an HPLC was 98.7%.
Workup
- customto return to room temperature
- additionThe resulting mixture was treated in the same manner as Example 8
Sources & evidence
- ORD record
- ord-6939cce387424616a600f480007b7159
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05648534
Reaction notes
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