Hydrochloric Acid → HCID 18982044, compound

HRID 2396485Notes

Reaction equation

B(F)(F)F.[BH4-].[Na+].[Cl:7][C:8]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:9]=1[CH2:10][N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[C:13](=O)[C:12]1([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:9]=1[CH2:10][N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][C:12]1([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

4.4 ml of freshly distilled boron trifluoride are added dropwise, while cold, to 1.1 g of dry sodium borohydride suspended in 35 ml of freshly distilled tetrahydrofuran. The reaction mixture is stirred at 0° C. for 2 hours and then 3.5 g (0.01 mol) of the compound obtained in Step g in 100 ml of tetrahydrofuran are added. The mixture is then heated under reflux for one hour and then 50 ml of a 2N hydrochloric acid solution are added while cold. The mixture is neutralised with sodium hydroxide and then extracted with ether. Customary treatment of the organic phase yields a crude product which is purified over a silica gel column (eluant: trichloromethane). 1 g of the pure desired product is obtained in the form of a colourless oil.

Workup

temperatureThe mixture is then heated
temperatureunder reflux for one hour
extractionextracted with ether
customCustomary treatment of the organic phase yields a crude product which
customis purified over a silica gel column (eluant: trichloromethane)

Sources & evidence

ORD record: ord-9ee5c39c40424b4a8d22a01077942c0f
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05492912

Reaction notes

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