Di-tert-butyl dicarbonate → HCID 131735925, compound

HRID 2207640Notes

Reaction equation

HRID 2207640 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]2[CH2:12][CH2:11][C@:10]3([CH2:16][CH2:15][N:14]([CH3:17])[C:13]3=[O:18])[NH:9]2)[C:3]=1[CH3:19].C(=O)(OC(C)(C)C)[O:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C@H:8]2[CH2:12][CH2:11][C@:10]3([CH2:16][CH2:15][N:14]([CH3:17])[C:13]3=[O:18])[N:9]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])[C:3]=1[CH3:19]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 89649170HCID 89649170, compound

Product 1

HCID 131735925HCID 131735925, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5R)-2-(4-bromo-3-methyl-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]nonan-6-one (which may be prepared as described in Description 10) (554.4 mg, 0.8500 mmol) in DCM (2 mL) was added and tert-butoxycarbonyl tert-butyl carbonate (373.2 mg, 1.71 mmol) the reaction was then stirred at room temperature for 3 days. The reaction was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with EtOAc in isohexane from 0% to 100%. A slower running material was isolated tert-butyl (2R,5R)-2-(4-bromo-3-methyl-2-pyridyl)-7-methyl-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (D98) (225.1 mg, 0.5305 mmol, 62% yield) as a colourless oil; M/Z: 423.8, 425.9 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with EtOAc in isohexane from 0% to 100%

Sources & evidence

ORD record
ord-5c05051bbe4b42a29a33f14e0f6a491f
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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