Hydrochloric Acid → HCID 57337070, compound

HRID 2403653Notes

Reaction equation

HRID 2403653 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[C:4](=[N:5][N:6]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:7]=2)[CH:3]1[O:30]C.CC(C)([O-])C.[K+].Cl>O1CCCC1.O>[C:26]([N:6]1[CH:7]=[C:8]2[C:4]([C:3](=[O:30])[CH2:2][C:10]3([CH2:9]2)[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12][CH2:11]3)=[N:5]1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 70654455HCID 70654455, compound

Product 1

HCID 57337070HCID 57337070, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 6-bromo-2-tert-butyl-7-methoxy-2,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carboxylate (150 mg, 0.31 mmol) was dissolved in 5 mL tetrahydrofuran and treated with potassium tert-butoxide (0.61 mL, 0.61 mmol, 1 M tetrahydrofuran) and stirred for 30 minutes. Aqueous 2 N HCl (5 mL) was added and the mixture was stirred for 15 minutes at room temperature. The mixture was then diluted with 50 mL water and extracted with ethyl acetate (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography (10-80% ethyl acetate/heptanes) to yield 86 mg (71%) of the title compound as a clear oil. +ESI (M+H) 396.5; 1H NMR (400 MHz, CDCl3, δ): 7.38 (s, 1 H), 7.27-7.35 (m, 5 H), 5.11 (s, 2 H), 3.48 (t, J=5.8 Hz, 4 H), 2.71 (s, 2 H), 2.57 (s, 2 H), 1.57-1.66 (m, 9 H), 1.47-1.59 (m, 4 H).

Workup

  1. stirringthe mixture was stirred for 15 minutes at room temperature
  2. extractionextracted with ethyl acetate (50 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (10-80% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-480491837ad64c7c93ee77f5fe7b528f
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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