Hydrochloric Acid → 7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride

HRID 241190Notes

Reaction equation

HRID 241190 reaction equation
[CH3:1][C:2]1([CH3:27])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:13]=3[CH:26]=2)[O:3]1.[ClH:28]>CO>[ClH:28].[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:27])[O:3][B:4]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][NH:15][CH2:14][C:13]=3[CH:26]=2)[O:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66820441Tert-butyl 7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine-4-carboxylate

Product 1

HCID 668206297-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochlorideYield 51.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a slurry of 1,1-dimethylethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (example 9, step 1) (3.3 g, 8.8 mmol) in methanol (25 mL) was added anhydrous hydrogen chloride (6.0 mL, 4 N in dioxane, 24 mmol). The reaction mixture was heated (60° C.) for 1.5 h and was concentrated. The resulting solid was suspended in ethyl ether (50 mL), collected by filtration and washed with ethyl ether (2×30 mL) to afford 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride (1.4 g, 50% yield) as a white solid. MS (EI) for C15H22BNO3: 276 (MH+).

Workup

  1. concentrationwas concentrated
  2. filtrationcollected by filtration
  3. washwashed with ethyl ether (2×30 mL)

Sources & evidence

ORD record
ord-fb12af780a0b441b94b79d316d075469
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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