Sodium cyanoborohydride → tert-Butyl 3-amino-7-bromo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

HRID 390154Notes

Reaction equation

HRID 390154 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:22]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[CH2:8][C:7]2=O.[BH3-]C#[N:26].[Na+]>CO>[NH2:26][CH:7]1[C:6]2[C:22](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=2)[C:9]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:8]1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 49760985Tert-butyl 7-bromo-3-oxo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 49760930tert-Butyl 3-amino-7-bromo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateYield 133.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl 7-bromo-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (196 mg, 0.52 mmol) in MeOH (20 mL) were added NH4OAc (795 mg, 10.3 mmol) and NaCNBH3 (324 mg, 5.2 mmol). The mixture was heated at reflux for 1 d. The mixture was concentrated under reduced pressure, diluted with EtOAc (90 mL), washed with 1M aq NaOH (25 mL) and dried over Na2SO4. Removal of the solvent gave crude (±)-tert-butyl 3-amino-7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (264 mg) which was used without purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 d
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additiondiluted with EtOAc (90 mL)
  5. washwashed with 1M aq NaOH (25 mL)
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-7d38a3dad2194de7895055e1111973c6
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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