Dibah → HCID 69157741, compound

Temperature

0 °C

To a 0° C. solution of methyl 4-[(t-butoxycarbonyl)-amino]-4-phenylbutanoate (293 mg, 1.0 mmol) in dichloromethane (25 mL) was added Dibal-H (3 mL of a 1.0 M solution in dichloromethane, 3.0 mmol). The mixture was then stirred at 0° C. for 2 hours before being quenched with a saturated aqueous sodium potassium tartrate solution (10 mL). The biphasic mixture was then rapidly stirred for approximately 45 minutes, until the aqueous and organic layers clarified. The aqueous and organic layers were then separated and the aqueous layer was extracted twice with dichloromethane. The combined organic fractions were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a pale yellow residue, which was purified by silica gel flash chromatography (1:1 hexanes:ethyl acetate) to afford 4-[(t-butoxycarbonyl)-amino]-4-phenylbutanol as a colourless oil in a yield of 138 mg (52%). 1H NMR (CDCl3) δ 1.43 (s, 9H), 1.45 (m, 2H), 1.56 (m 2H), 2.71 (br s, 1H (OH)), 3.54 (t, 2H, J=6.9 Hz), 4.56 (m, 1H), 5.22 (br s, 1H (NH)), 7.16-7.26 (m, 5H).

1. custombefore being quenched with a saturated aqueous sodium potassium tartrate solution (10 mL)
2. stirringThe biphasic mixture was then rapidly stirred for approximately 45 minutes
3. customThe aqueous and organic layers were then separated
4. extractionthe aqueous layer was extracted twice with dichloromethane
5. dry with materialThe combined organic fractions were dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto afford a pale yellow residue, which
9. customwas purified by silica gel flash chromatography (1:1 hexanes:ethyl acetate)

ORD record

ord-f2c1c4671eaa4ad2b810e9d5e482dde4

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354934B2