Sodium borohydride → Tert-butyl (1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl)carbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH3:24])[CH:15]=1)[CH2:10][C:11](=[O:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH3:24])[CH:15]=1)[CH2:10][CH:11]([OH:13])[CH3:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -15 °C
Procedure
A mixture of (tert-butoxy)-N-[1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]carboxamide (2.0 g, 5.92 mmol) and sodium borohydride (0.4 g, 12.0 mmol) in methanol (40 mL) and tetrahydrofuran (10 mL) was stirred at −10 to −20° C. for 4 hours. The mixture was quenched with water (10 mL) and then concentrated in vacuo to afford an oil. The oil was dissolved in ethyl acetate and washed with water, brine, dried, and concentrated in vacuo to afford an oil. The oil was purified by chromatography (silica gel, methylene chloride:ethyl acetate 8:2) to give the two diasteromers of (tert-butoxy)-N-[1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl)carboxamide:
Workup
- customThe mixture was quenched with water (10 mL)
- concentrationconcentrated in vacuo
- customto afford an oil
- washwashed with water, brine
- customdried
- concentrationconcentrated in vacuo
- customto afford an oil
- customThe oil was purified by chromatography (silica gel, methylene chloride:ethyl acetate 8:2)
Sources & evidence
- ORD record
- ord-24bf0962dce54ce39a4ea1521ed8a191
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06667316B1
Reaction notes
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