Sodium Tetrafluoroborate → Dibenzylhydroxylamine

HRID 1708336Notes

Reaction equation

HRID 1708336 reaction equation
[O:1]([N:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[Si](C(C)(C)C)(C)C.F[B-](F)(F)F.[Na+]>>[CH2:17]([N:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[OH:1])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 4343483Sodium TetrafluoroborateHCID 15219400HCID 15219400, compound

Product 1

HCID 69297DibenzylhydroxylamineYield 82%

Procedure

tert-Butyldimethylsiloxy-N,N-dibenzylamine, Compound 1, was heated with sodium tetrafluoroborate at about 200° C. for 30 minutes. The tert-butyldimethylfluorosilane could be distilled off at 62°-64° C. in 82% yield. N,N-dibenzylhydroxylamine was isolated from the reaction. Similar results were obtained using sodium salts of hexafluorophosphate and hexafluoroantimonate.

Workup

  1. distillationThe tert-butyldimethylfluorosilane could be distilled off at 62°-64° C. in 82% yield

Sources & evidence

ORD record
ord-b27a97d95ac2474980480dfa4329a26b
Source dataset
uspto-grants-1994_10
Patent number
US05358843

Reaction notes

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