Ammonia → tert-Butyl 2,3-dihydro-1H,1'H-spiro[isoquinoline-4,4'-piperidine]-1'-carboxylate

HRID 266897Notes

Reaction equation

HRID 266897 reaction equation
O[CH:2]1[C:6]2=[CH:7][CH:8]=[CH:9][C:10]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)[CH:5]2[CH:4](O)O1.[NH3:24].[CH3:25]O>>[N:13]1([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:14][CH2:15][C:10]2([C:5]3[C:6](=[CH:7][CH:8]=[CH:25][CH:4]=3)[CH2:2][NH:24][CH2:9]2)[CH2:11][CH2:12]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 131719466HCID 131719466, compound

Product 1

HCID 46942140tert-Butyl 2,3-dihydro-1H,1'H-spiro[isoquinoline-4,4'-piperidine]-1'-carboxylate

Procedure

The intermediate of Step A (100 mg) was stirred in methanol (2 mL) saturated with ammonia for one day, and evaporated to remove ammonia. The residue was redissolved in methanol (3 mL) and sodium cyanoborohydride (50 mg, excess) was added. The mixture was stirred overnight. Evaporation and purification gave the amine.

Workup

  1. customevaporated
  2. customto remove ammonia
  3. dissolutionThe residue was redissolved in methanol (3 mL)
  4. additionsodium cyanoborohydride (50 mg, excess) was added
  5. customEvaporation and purification

Sources & evidence

ORD record
ord-eabe6aa4009e4d5888bf3c71cc03a019
Source dataset
uspto-grants-1997_07
Patent number
US05652235

Reaction notes

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