Diisobutylaluminum hydride → Tert-butyl ((4-(hydroxymethyl)oxazol-2-yl)methyl)carbamate

HRID 8906

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

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-98cbae85125a4e74a5cd6403dc05c603
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091217B2

Linked notes

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