Ammonium Chloride → tert-Butyl 6-cyano-4-hydroxy-spiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 1096921Notes

Reaction equation

HRID 1096921 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:22](=[CH:23][CH:24]=1)[O:21][C:8]1([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[CH2:7][C:6]2=[O:25])#[N:2].[BH4-].[Na+].[NH4+].[Cl-]>CCO.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:22](=[CH:23][CH:24]=1)[O:21][C:8]1([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[CH2:7][CH:6]2[OH:25])#[N:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 66649586Tert-butyl 6-cyano-4-oxo-3,4-dihydrospiro[1-benzopyran-2,4'-piperidine]-1'-carboxylate

Product 1

HCID 66649142tert-Butyl 6-cyano-4-hydroxy-spiro[chroman-2,4'-piperidine]-1'-carboxylate

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 15 g of tert-butyl 6-cyano-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate in 250 mL of EtOH-THF(1:4) at 0° C. was added NaBH4 portionwise, and the reaction mixture was allowed to warm up to rt. After stirring for 1 h, NH4Cl aqueous was added to the reaction mixture and the aqueous mixture was extracted with AcOEt twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in reduced pressure to give the intended compound as a pale yellow solid.

Workup

  1. extractionthe aqueous mixture was extracted with AcOEt twice
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in reduced pressure

Sources & evidence

ORD record
ord-e7d84f57c9d248509eddb5e8ef418e95
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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