Sodium Sulfate → 2-Amino-2-(3-bromophenyl)propan-1-ol

HRID 1912449Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]([NH2:19])([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=1)[CH3:11].[O-]S([O-])(=O)=O.[Na+].[Na+].[H][H]>C1COCC1>[NH2:19][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=1)([CH3:11])[CH2:9][OH:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminium hydride (1 M in THF; 22 mL, 22 mmol) was added dropwise to a stirred solution of rac-2-amino-2-(3-bromo-phenyl)-propionic acid methyl ester (7.5 g, 29.1 mmol) in THF (200 mL) at −15° C. The mixture was left warming up slowly to 0° C. during 1 hour. Then more THF (150 mL) was added and sat. Na2SO4 was added dropwise until no more hydrogen was formed. Then anhydrous Na2SO4 was added and left stirring overnight at room temperature. The mixture was filtered over diatomaceous earth, rinsed with THF and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 7 M solution of ammonia in methanol in DCM 0/100 to 3/97). The desired fractions were collected and concentrated in vacuo to yield rac-2-amino-2-(3-bromo-phenyl)-propan-1-ol (5.70 g, 85% yield) as an oil.

Workup

waitThe mixture was left
customwas formed
waitleft
filtrationThe mixture was filtered over diatomaceous earth
washrinsed with THF
customthe solvent evaporated in vacuo
customThe crude product was purified by flash column chromatography (silica gel; 7 M solution of ammonia in methanol in DCM 0/100 to 3/97)
customThe desired fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-efec8c12963a4cf1ace57604118b7a71
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609660B2

Reaction notes

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