Water → racemic (5S*,6R*)-6-azido-5-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carbonitrile
Reaction equation
[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([C:14]#[N:15])[CH:8]=[CH:7][C:6]=2[C:5]1=[O:16])=[N+:2]=[N-:3].O.[BH4-].[Na+]>C1COCC1>[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([C:14]#[N:15])[CH:8]=[CH:7][C:6]=2[CH:5]1[OH:16])=[N+:2]=[N-:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Racemic 6-azido-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (28 mg, 0.13 mmol) was dissolved in THF (1253 mL) and water (66.0 mL) at 0° C. To this solution was added sodium borohydride (6.49 mg, 0.17 mmol). The resulting solution was stirred at 0° C. for 45 min. After that, the reaction was quenched by several drops of 1N HCl. The mixture was loaded to an ISCO 13 g column directly and purified by ISCO Combiflash Companion (10% ethyl acetate-hexane for 3 min then ramp to 50% ethyl acetate-hexane over 7 min then 20% ethyl acetate-hexane for 5 more min, product came out 8-10 min) to afford racemic (5S*,6R*)-6-azido-5-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (15.0 mg, 0.07 mmol, 53.1%) as a white solid. NMR showed that the product was a mixture of around 6:1 two diastereomers; LCMS=215.22 [M+H]+.
Workup
- customat 0° C
- customAfter that, the reaction was quenched by several drops of 1N HCl
- custompurified by ISCO Combiflash Companion (10% ethyl acetate-hexane for 3 min
- waitthen ramp to 50% ethyl acetate-hexane over 7 min
- wait20% ethyl acetate-hexane for 5 more min, product came out 8-10 min
Sources & evidence
- ORD record
- ord-f65639ccc0534e44819a8fcf018d9436
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629282B2
Reaction notes
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