Tetrahydrofuran → tert-butyl (1R,2S)-1-hydroxy-1-m-tolylpropan-2-ylcarbamate

HRID 13030Notes

Reaction equation

HRID 13030 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].[C:17]1([CH3:25])[CH:22]=[CH:21][CH:20]=[C:19]([Mg]Br)[CH:18]=1.C1COCC1>>[OH:15][C@H:4]([C:19]1[CH:18]=[C:17]([CH3:25])[CH:22]=[CH:21][CH:20]=1)[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH3:6]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178425413HCID 178425413, compound

Product 1

HCID 59339884tert-butyl (1R,2S)-1-hydroxy-1-m-tolylpropan-2-ylcarbamate

Procedure

The subtitle compound was prepared in two steps analogous to the methods described in Example 19 (step 19c+19d). Starting from (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (2.323 g, 10 mmol), and m-tolylmagnesium bromide 1.0M solution in THF (12.00 mL, 12.00 mmol). Yield 2.33 g (88%)

Sources & evidence

ORD record
ord-5cf924039e0d424c87afad66d6350ace
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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