Nitrilooxonium tetrafluoroborate → HCID 58123510, compound

HRID 1616658Notes

Reaction equation

HRID 1616658 reaction equation
[F:1][B-](F)(F)F.N#[O+].C(OC([N:15]1[CH2:22][CH2:21][C@:20]2([CH3:26])[C:23]([CH3:25])([CH3:24])[C@H:16]1[CH2:17][C:18]1[C:30](N)=[CH:29][CH:28]=[CH:27][C:19]=12)=O)(C)(C)C>O1CCOCC1.CO>[F:1][C:30]1[C:18]2[CH2:17][C@@H:16]3[C:23]([CH3:25])([CH3:24])[C@:20]([CH3:26])([C:19]=2[CH:27]=[CH:28][CH:29]=1)[CH2:21][CH2:22][NH:15]3

Participants

5

Reactant 2

HCID 11137142Nitrilooxonium tetrafluoroborateHCID 58123706HCID 58123706, compound

Product 1

HCID 58123510HCID 58123510, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of nitrosonium tetrafluoroborate (0.25 g) in 1,4-dioxane (2 mL) is added to a solution of (2R,6S)-10-amino-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carboxylic acid tert-butyl ester (0.10 g) in dioxane (2 mL). The solution is heated to 50° C. and stirred at this temperature overnight. The reaction solution is diluted with methanol and then concentrated under reduced pressure. The residue is purified by HPLC on reversed phase (MeCN/H2O/F3CCO2H) to yield the title product.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified by HPLC on reversed phase (MeCN/H2O/F3CCO2H)

Sources & evidence

ORD record
ord-a3451c2e998545978db05447f05f10bf
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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