Hydrochloric Acid → (2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepin-7-yl)boronic acid hydrochloride

HRID 241165Notes

Reaction equation

HRID 241165 reaction equation
CC(OC([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([B:19]([OH:21])[OH:20])[CH:17]=[CH:18][C:12]=2[O:11][CH2:10][CH2:9]1)=O)(C)C.[ClH:22]>O1CCOCC1.C(OCC)C>[ClH:22].[O:11]1[C:12]2[CH:18]=[CH:17][C:16]([B:19]([OH:21])[OH:20])=[CH:15][C:13]=2[CH2:14][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59604707(4-(Tert-butoxycarbonyl)-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-7-yl)boronic acid

Product 1

HCID 66820605(2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepin-7-yl)boronic acid hydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

(4-{[(1,1-dimethylethyl)oxycarbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)boronic acid (Example 1, step 2) (1.07 g, 3.64 mmol) was dissolved into 4M hydrogen chloride in dioxane and the resulting solution was allowed to stir at room temperature for 1.3 h. The heterogeneous mixture was then diluted with ethyl ether (100 mL) and the solid collected by filtration to give 2,3,4,5-tetrahydro-1,4-benzoxazepin-7-ylboronic acid hydrochloride salt (791 mg, 95%). 1H NMR (400 MHz, D2O): 7.79 (dd, 1H), 7.74 (d, 1H), 7.21 (d, 1H), 4.47 (s, 2H), 4.36 (m, 2H), 3.69 (m, 2H).

Workup

  1. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-ba95f8b2f2934dc4beb281cb07532f1c
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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