Triethylamine → Benzyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate

HRID 634428Notes

Reaction equation

HRID 634428 reaction equation
[CH3:1][C:2]1([CH3:24])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH2:15][CH:14]3[N:16]([C:17]([O:19]C(C)(C)C)=[O:18])[CH:11]([CH2:12][CH2:13]3)[CH:10]=2)[O:3]1.O1CCOCC1.Cl.[CH2:32](OC(ON1C(=O)CCC1=O)=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C>O1CCOCC1.CCOC(C)=O.CCCCCCC>[CH3:24][C:2]1([CH3:1])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH2:15][CH:14]3[N:16]([C:17]([O:19][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:18])[CH:11]([CH2:12][CH2:13]3)[CH:10]=2)[O:3]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 204431481,4-Dioxane hydrochlorideHCID 53393373Tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo(3.2.1)oct-2-ene-8-carboxylate

Product 1

HCID 72206714Benzyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylateYield 38.1%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (Intermediate G21.2, 1.93 g, 5.76 mmol) in dry Dioxane (20 ml), 4 M hydrogen chloride 1,4 dioxane (5.76 ml, 23.03 mmol) was added and the solution was stirred for 1 h. Then, solvent was removed. Crude was dissolved in dry DCM (20.00 ml), N-(benzyloxycarbonyloxy)succinimide (1.964 ml, 6.91 mmol) and triethylamine (3.14 ml, 23.03 mmol) were added and the suspension was stirred for 1 h. Then, solvent was removed and the product was purified by Biotage Si 25 g with a gradient of heptane and EtOAc affording the title compound (810 mg, 2.194 mmol, 38.1% yield) as a white solid.

Workup

  1. customThen, solvent was removed
  2. dissolutionCrude was dissolved in dry DCM (20.00 ml)
  3. stirringthe suspension was stirred for 1 h
  4. customThen, solvent was removed

Sources & evidence

ORD record
ord-6908fee832b04961ac8e4771a7d41c82
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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