(2R,6R,11S)-6,11-dimethyl-8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carboxylic acid tert-butyl ester → (2R,6R,11S)-6,11-Dimethyl-8-borono-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carboxylic acid tert-butyl ester

HRID 536664Notes

Reaction equation

HRID 536664 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C@:13]2([CH3:18])[C@H:16]([CH3:17])[C@H:9]1[CH2:10][C:11]1[CH:22]=[CH:21][C:20]([B:23]3[O:27]C(C)(C)C(C)(C)[O:24]3)=[CH:19][C:12]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C@:13]2([CH3:18])[C@H:16]([CH3:17])[C@H:9]1[CH2:10][C:11]1[CH:22]=[CH:21][C:20]([B:23]([OH:27])[OH:24])=[CH:19][C:12]=12)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 58123692(2R,6R,11S)-6,11-dimethyl-8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carboxylic acid tert-butyl ester

Product 1

HCID 58123740(2R,6R,11S)-6,11-Dimethyl-8-borono-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (2R,6R,11S)-6,11-dimethyl-8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carboxylic acid tert-butyl ester (2.50 g) and NaIO4 (5.00 g) in 1 M aqueous NH4OAc solution (34 mL) and acetone (60 mL) is stirred at room temperature overnight. Then, the solution is concentrated, water is added to the residue, and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed with water and brine and dried (Na2SO4). The solvent is removed under reduced pressure to give the title compound as a colorless, foam-like solid.

Workup

  1. concentrationThen, the solution is concentrated
  2. additionwater is added to the residue
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. washThe combined organic extracts are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-6d390908c0fe4ea6b81b8a503813e003
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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