Diisobutylaluminum hydride → Tert-butyl ((4-(hydroxymethyl)oxazol-2-yl)methyl)carbamate
Reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[O:8][CH:9]=1)=O.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl>[C:15]([O:14][C:12](=[O:13])[NH:11][CH2:10][C:7]1[O:8][CH:9]=[C:5]([CH2:3][OH:2])[N:6]=1)([CH3:18])([CH3:16])[CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The ester (178 mg, 0.695 mmol) in 0° C. dichloromethane (8 mL) was treated with DIBAL-H (1 M in dichloromethane, 2.08 mL, 2.08 mmol). The mixture was then stirred at 0° C. for 2 hours before being treated with aqueous 5% sodium potassium tartrate (8 mL). The mixture was stirred rapidly for 30 minutes (until the aqueous and organic layers clarified), and the layers were then separated. The aqueous layer was extracted twice with dichloromethane. The combined organic fractions were then dried over anhydrous sodium sulfate and concentrated. Purification by chromatography on silica gel (5% methanol in dichloromethane) gave (4-hydroxymethyl-oxazol-2-ylmethyl)-carbamic acid tert-butyl ester as an oil (45 mg, 28%). 1H NMR (CDCl3) δ 1.40 (s, 9H), 4.43 (d, 2H, J=5.6 Hz), 4.56 (s, 2H), 5.37 (s, 1H), 7.54 (s, 1H).
Workup
- stirringThe mixture was stirred rapidly for 30 minutes (until the aqueous and organic layers
- customwere then separated
- extractionThe aqueous layer was extracted twice with dichloromethane
- dry with materialThe combined organic fractions were then dried over anhydrous sodium sulfate
- concentrationconcentrated
- customPurification by chromatography on silica gel (5% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-f816e08cdf00484586c4294ef4fd71e8
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807694B2
Reaction notes
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