Sodium borohydride → {3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzyl}-methyl-amine

HRID 1295732Notes

Reaction equation

[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH:13]=[N:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CCO>[C:1]([Si:5]([CH3:19])([CH3:20])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][NH:14][CH3:15])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzylidene}-methyl-amine (1.174 g, 4.00 mmol) was dissolved in EtOH and cooled to 0° C. NaBH4 (189 mg, 5.00 mmol) was added and the mixture was allowed to stir for 4 h. The reaction was carefully quenched with water. The EtOH was removed in vacuo. The aqueous residue was extracted with CH2Cl2. The organic extracts were dried over Na2SO4 and concentrated in vacuo to give 1.185 g (quant) of a white powder.

Workup

customThe reaction was carefully quenched with water
customThe EtOH was removed in vacuo
extractionThe aqueous residue was extracted with CH2Cl2
dry with materialThe organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customto give 1.185 g (quant) of a white powder

Sources & evidence

ORD record: ord-d7e350a851a94a2aa9cc78c2d3f23347
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244738B2

Reaction notes

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