Hydrochloric Acid → HCID 57451824, compound

HRID 339638Notes

Reaction equation

HRID 339638 reaction equation
[N:1]([CH2:4][C@@:5]1([CH3:15])[O:9][B:8]([OH:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]1=2)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[ClH:35]>C(#N)C>[ClH:35].[NH2:1][CH2:4][C@@:5]1([CH3:15])[O:9][B:8]([OH:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 57451826HCID 57451826, compound

Product 1

HCID 57451824HCID 57451824, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-3-(azidomethyl)-3-methylbenzo[c][1,2]oxaborol-1(3H)-ol (700 mg, 3.45 mmol) and triphenyl phosphine (1.8 g, 6.9 mmol) were dissolved in 35 mL of acetonitrile. After 5 min concentrated hydrochloric acid (6.9 mL) was added and the reaction mixture was stirred for 24 hrs at room temperature before being concentrated under vacuum. The residue was taken up in DCM and washed 3× with 20 mL of 2M HCl. The combined aqueous layers were evaporated to dryness under vacuum. The resulting solid was washed with EtOH and filtered to remove byproducts, concentrated and crystallized from acetonitrile to give 160 mg (20%) of (S)-3-(aminomethyl)-3-methylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride as a white solid.

Workup

  1. concentrationbefore being concentrated under vacuum
  2. washwashed 3× with 20 mL of 2M HCl
  3. customThe combined aqueous layers were evaporated to dryness under vacuum
  4. washThe resulting solid was washed with EtOH
  5. filtrationfiltered
  6. customto remove byproducts
  7. concentrationconcentrated
  8. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-b77e266a147648558a906c04e3b384c3
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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