Potassium Carbonate → 1'-Methyl-6,7-dihydro-2H,5H-spiro[furo[2,3-f]indole-3,4'-piperidine]

HRID 1741035Notes

Reaction equation

HRID 1741035 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:18]3[CH2:17][C:16]4[C:12]([CH:13]=[CH:14][N:15]=4)=[CH:11][C:10]=3[O:9][CH2:8]2)[CH2:4][CH2:3]1.C([BH3-])#N.[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.O>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([C:18]3[C:10](=[CH:11][C:12]4[CH2:13][CH2:14][NH:15][C:16]=4[CH:17]=3)[O:9][CH2:8]2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 701980042,3-Dihydro-1'-methylspiro[furo[2,3-f]indole-3,4'-piperidine]

Product 1

HCID 106579521'-Methyl-6,7-dihydro-2H,5H-spiro[furo[2,3-f]indole-3,4'-piperidine]Yield 53.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2,3-Dihydro-1'-methylspiro[furo[2,3-f]indole-3,4'-piperidine] (D7, 0.056 g, 0.23 mmol) was stirred in acetic acid (5 ml) as sodium cyanoborohydride (0.044 g, 0.70 mmol) was added portionwise over 10 min. The solution was stirred for 2 h, diluted with water (20 ml), basified with saturated K2CO3 solution, and extracted with ethyl acetate. The extract was dried (Na2SO4) and evaporated to give the title compound (0.030 g, 53%) as a white solid.

Workup

  1. additionwas added portionwise over 10 min
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-718a178f862c4860900ec628b0e02d55
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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