Tetrahydrofuran → (S)-tert-butyl 1-(3-ethylphenyl)-1-oxopropan-2-ylcarbamate

HRID 13028Notes

Reaction equation

HRID 13028 reaction equation
CON(C)[C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].[CH2:17]([C:19]1[CH:20]=[C:21]([Mg]Br)[CH:22]=[CH:23][CH:24]=1)[CH3:18].C1COCC1>>[CH2:17]([C:19]1[CH:24]=[C:23]([C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH3:6])[CH:22]=[CH:21][CH:20]=1)[CH3:18]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178436338HCID 178436338, compound

Product 1

HCID 59339663(S)-tert-butyl 1-(3-ethylphenyl)-1-oxopropan-2-ylcarbamate

Procedure

The subtitle compound was prepared analogous to the method described in Example 19 (step 19d). Starting from (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (0.7 g, 3.01 mmol) and freshly made (3-ethylphenyl)magnesium bromide 0.9M solution in THF (5 mL, 4.50 mmol). Yield 817 mg (97%)

Sources & evidence

ORD record
ord-99f35be9b4874ec3accc08ee17beeb82
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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