Potassium Carbonate → HCID 67224229, compound

HRID 390155Notes

Reaction equation

HRID 390155 reaction equation
[NH2:1][CH:2]1[C:22]2[C:17](=[C:18]([Br:23])[CH:19]=[CH:20][CH:21]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH2:3]1.C([O-])([O-])=O.[K+].[K+].[C:30](ON1C(=O)CCC1=O)([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:31]>C1COCC1.CCOCC>[Br:23][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:17]=1[C:4]1([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH2:3][CH:2]2[NH:1][C:30]([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 49760930tert-Butyl 3-amino-7-bromo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 67224229HCID 67224229, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of crude (±)-tert-butyl 3-amino-7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (264 mg, 0.69 mmol) in THF (5 mL) was added 10% aq K2CO3 (10 mL), followed by Teoc-OSu (269 mg, 1.04 mmol). The mixture was stirred at rt for 3 d, diluted with ether (80 mL), washed with brine (25 mL) and dried over MgSO4. Removal of the solvent left an oil (240 mg) which was purified chromatography on a 12-g silica cartridge, eluted with a 0-50% EtOAc in hexanes gradient to afford (±)-tert-butyl 7-bromo-3-((2-(trimethylsilyl)ethoxy)carbonylamino)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (85 mg, 31% for 2 steps). LC-MS Method 1 tR=2.35 min, m/z=425, 427, 547, 549.

Workup

  1. washwashed with brine (25 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent
  4. waitleft an oil (240 mg) which
  5. customwas purified chromatography on a 12-g silica cartridge
  6. washeluted with a 0-50% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-2c0c80839e32486aaf4a96a411392b9c
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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