Ammonium Chloride → HCID 58252526, compound

HRID 2403658Notes

Reaction equation

HRID 2403658 reaction equation
Br[CH:2]1[C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:12][CH2:11]2)[CH2:9][C:8]2[CH:7]=[N:6][N:5]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:4]=2[C:3]1=[O:30].[Cl-].[NH4+]>O1CCCC1.[Zn]>[C:26]([N:5]1[C:4]2[C:3](=[O:30])[CH2:2][C:10]3([CH2:11][CH2:12][N:13]([C:16]([O:18][CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[O:17])[CH2:14][CH2:15]3)[CH2:9][C:8]=2[CH:7]=[N:6]1)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58252469HCID 58252469, compound

Product 1

HCID 58252526HCID 58252526, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 6-bromo-1-tert-butyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carboxylate (50.4 g, 106 mmol) in tetrahydrofuran (600 mL), was added saturated aqueous ammonium chloride (600 mL) and zinc powder (20.8 g, 319 mmol). The reaction was stirred for 30 minutes at room temperature. The reaction was filtered through Celite®. The phases of the filtrate were separated and the organic phase was washed with water and saturated aqueous sodium chloride. The organics were dried over magnesium sulfate, filtered, and concentrated to provide a foam. The foam was triturated once with ethyl acetate/heptanes and once with diethylether to afford the title compound (40.4 g, 96%) as a white solid. +ESI (M+H) 396.5; 1H NMR (400 MHz, CDCl3, δ): 7.24-7.38 (m, 6H), 5.11 (s, 2 H), 3.36-3.61 (m, 4 H), 2.74 (s, 2 H), 2.54 (s, 2 H), 1.64 (s, 9 H), 1.51 (br. s., 4 H).

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. customThe phases of the filtrate were separated
  3. washthe organic phase was washed with water and saturated aqueous sodium chloride
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a foam
  8. customThe foam was triturated once with ethyl acetate/heptanes and once with diethylether

Sources & evidence

ORD record
ord-315041dcb1544317a7ba87604052f3ed
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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