Sodium borohydride → Tert-butyl 5-chlorospiro[indoline-3,4'-piperidine]-1'-carboxylate

HRID 529051Notes

Reaction equation

HRID 529051 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH:11]=[N:10][C:7]2=[CH:8][CH:9]=1>CCO>[Cl:3][C:4]1[CH:5]=[C:6]2[C:12]3([CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]3)[CH2:11][NH:10][C:7]2=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67374111Tert-butyl 5-chlorospiro[indole-3,4'-piperidine]-1'-carboxylate

Product 1

HCID 46835581Tert-butyl 5-chlorospiro[indoline-3,4'-piperidine]-1'-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (1.29 g, 34.0 mmol) was added to a stirred solution of tert-butyl 5-chlorospiro[indole-3,4′-piperidine]-1′-carboxylate (2.57 g, 8.01 mmol) in absolute EtOH (100 mL) portionwise. The reaction was stirred at about room temperature overnight. The reaction was concentrated. The crude residue was taken up in DCM, washed with water and brine, dried over MgSO4, filtered, and concentrated. The crude residue was purified by column chromatography (25-35% EtOAc/Hexane) to yield tert-butyl 5-chlorospiro[indoline-3,4′-piperidine]-1′-carboxylate. LCMS (APCI+) m/z 223, 225 [M+H−Boc]+; Rt=3.86 min.

Workup

  1. concentrationThe reaction was concentrated
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by column chromatography (25-35% EtOAc/Hexane)

Sources & evidence

ORD record
ord-0a6898abdfc146adac94be8dd6f520cf
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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