Tetrahydrofuran → tert-butyl [(1S)-1-methyl-2-(2-naphthyl)-2-oxoethyl]carbamate

HRID 13024Notes

Reaction equation

HRID 13024 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].[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[Mg]Br.C1COCC1>>[C:10]([O:9][C:8](=[O:14])[NH:7][C@@H:5]([CH3:6])[C:4]([C:19]1[CH:18]=[CH:17][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)=[O:15])([CH3:11])([CH3:12])[CH3:13]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178418423HCID 178418423, compound

Product 1

HCID 59339838tert-butyl [(1S)-1-methyl-2-(2-naphthyl)-2-oxoethyl]carbamate

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 (1.86 g, 8 mmol) and a freshly prepared 2-Naphthylmagnesiumbromide 1M solution in THF (8 mL, 8 mmol). The obtained material was crystallised from Heptane. Yield 350 mg (14%).

Workup

  1. customThe obtained material was crystallised from Heptane

Sources & evidence

ORD record
ord-94c704e41ce44a75a87597d3c55b1022
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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