Water → racemic (3R*,4S*)-3-azido-4-hydroxychroman-7-carbonitrile

HRID 470582Notes

Reaction equation

HRID 470582 reaction equation
[N:1]([CH:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][C:9]([C:15]#[N:16])=[CH:10][CH:11]=2)[O:6][CH2:5]1)=[N+:2]=[N-:3].O.[BH4-].[Na+]>C1COCC1>[N:1]([CH:4]1[CH:13]([OH:14])[C:12]2[C:7](=[CH:8][C:9]([C:15]#[N:16])=[CH:10][CH:11]=2)[O:6][CH2:5]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 89799702Racemic 3-azido-4-oxochroman-7-carbonitrile

Product 1

HCID 131731133racemic (3R*,4S*)-3-azido-4-hydroxychroman-7-carbonitrileYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Racemic 3-azido-4-oxochroman-7-carbonitrile Int-2-B (2.30 g, 10.8 mmol) was dissolved in THF (103 mL) and water (5.42 mL) at 0° C. To this solution was added sodium borohydride (0.53 g, 14.1 mmol). The reaction mixture was stirred at 0° C. for 45 mins. Next, the reaction was quenched by addition of 1N HCl. The resulting solution was extracted with EtOAc and washed with water and brine. The organic layers were combined, dried (MgSO4) and concentrated to give racemic (3R*,4S*)-3-azido-4-hydroxychroman-7-carbonitrile Int-2-C (2.21 g, 10.2 mmol, 94.3% yield): LCMS=217.06 [M+H]+.

Workup

  1. customat 0° C
  2. customNext, the reaction was quenched by addition of 1N HCl
  3. extractionThe resulting solution was extracted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1538629aac5441ac92a082d06397cd18
Source dataset
uspto-grants-2014_01
Patent number
US08629282B2

Reaction notes

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