(3S,4S)-3-Aminotetrahydro-2H-pyran-4-OL → HCID 118468216, compound

HRID 629467Notes

Reaction equation

HRID 629467 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([CH2:7][C:8]2[C:9]([CH3:21])=[C:10]([CH3:20])[C:11]([CH:18]=O)=[C:12]([CH:17]=2)[C:13](OC)=[O:14])=[CH:5][C:4]=1[F:24])#[N:2].[NH2:25][C@@H:26]1[C@@H:31]([OH:32])[CH2:30][CH2:29][O:28][CH2:27]1>C1COCC1>[C:1]([C:3]1[CH:23]=[CH:22][C:6]([CH2:7][C:8]2[CH:17]=[C:12]3[C:11]([CH2:18][N:25]([C@@H:26]4[C@@H:31]([OH:32])[CH2:30][CH2:29][O:28][CH2:27]4)[C:13]3=[O:14])=[C:10]([CH3:20])[C:9]=2[CH3:21])=[CH:5][C:4]=1[F:24])#[N:2]

Participants

4

Reactant 2

HCID 55285677(3S,4S)-3-Aminotetrahydro-2H-pyran-4-OLHCID 118468115HCID 118468115, compound

Product 1

HCID 118468216HCID 118468216, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(4-cyano-3-fluorobenzyl)-2-formyl-3,4-dimethylbenzoate (0.25 g) in THF (5.00 mL) was added (3S,4S)-3-aminotetrahydro-2H-pyran-4-ol (0.09 g), and the mixture was stirred overnight at room temperature under argon atmosphere. The reaction mixture was concentrated, and the residue was diluted with acetic acid (5.00 mL). Then, sodium triacetoxyborohydride (0.24 g) was added thereto and the mixture was stirred at room temperature for 2 hr under argon atmosphere. To the reaction mixture was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane, methanol/ethyl acetate) to give the title compound (0.16 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with acetic acid (5.00 mL)
  3. additionThen, sodium triacetoxyborohydride (0.24 g) was added
  4. stirringthe mixture was stirred at room temperature for 2 hr under argon atmosphere
  5. additionTo the reaction mixture was added saturated aqueous sodium bicarbonate
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane, methanol/ethyl acetate)

Sources & evidence

ORD record
ord-5df43b6700404f11a1368661354fa91a
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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