Triethylamine → 7-Boc-9-Cbz-3-oxa-7,9-diazabicyclo[3.3.1]nonane

HRID 1778544Notes

Reaction equation

HRID 1778544 reaction equation
[CH:1]12[NH:16][CH:5]([CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8]1)[CH2:4][O:3][CH2:2]2.C(N(CC)CC)C.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>ClCCl>[CH:5]12[N:16]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH:1]([CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:6]1)[CH2:2][O:3][CH2:4]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 53415349tert-Butyl 3-oxa-7,9-diazabicyclo(3.3.1)nonane-7-carboxylate

Product 1

HCID 1176981007-Boc-9-Cbz-3-oxa-7,9-diazabicyclo[3.3.1]nonaneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate (0.500 g, 2.2 mmol) in dichloromethane (5 ml) was added triethylamine (0.443 g, 4.4 mmol) at room temperature. The mixture was stirred at room temperature for a few mins, and then benzyl chloroformate (0.751 g, 4.4 mmol) was added to the reaction mixture. The resulting mixture was stirred at room temperature overnight. The mixture was partitioned between dichloromethane and water. The organic phase was dried, and concentrated. The residue was purified by silica gel chromatography to give 9-benzyl 7-tert-butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7,9-dicarboxylate 133b (0.637 g, 80.0%). MS: calc'd (MH+) 363, measured (MH+) 363.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customThe mixture was partitioned between dichloromethane and water
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f13193c56c164872b5c85dc6bc3ebf5e
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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