Triethylamine → HCID 89738587, compound

HRID 592052Notes

Reaction equation

HRID 592052 reaction equation
[NH2:1][C@@H:2]1[C@@H:7]2[O:8][C@@H:4]([CH2:5][CH2:6]2)[C@@H:3]1[C:9]([O:11][CH3:12])=[O:10].CCN(CC)CC.[O:20](C(OC(C)(C)C)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O>C(#N)C>[C:24]([O:23][C:21]([NH:1][C@@H:2]1[C@@H:7]2[O:8][C@@H:4]([CH2:5][CH2:6]2)[C@@H:3]1[C:9]([O:11][CH3:12])=[O:10])=[O:20])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 89738585rel-Methyl (1R,2S,3R,4S)-3-amino-7-oxabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 89738587HCID 89738587, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (1S,2R,3S,4R)-methyl 3-amino-7-oxabicyclo[2.2.1]heptane-2-carboxylate (11) (500 mg, 2.4 mmol), Et3N (0.85 ml, 6 mmol) and BOC2O (0.66 ml, 2.88 mmol) in acetonitrile was stirred at rt for 2 h and then heated at 80° C. for 30 min when TLC confirmed completion of reaction. Acetonitrile was removed and the crude product was purified by column chromatography using silica gel (100-200 mesh) to afford the desired compound (600 mg, 92%) as a colourless oil.

Workup

  1. customcompletion of reaction
  2. customAcetonitrile was removed
  3. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-56f1d53e5692499fb547b8ddc7e5ddf1
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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