HCID 118161615, compound → HCID 118161656, compound

HRID 2203681Notes

Reaction equation

HRID 2203681 reaction equation
CON(C)[C:4]([CH:6]1[CH:14]2[CH:7]1[CH2:8][C:9]1([CH2:13]2)[CH2:12][O:11][CH2:10]1)=[O:5].[CH3:16][Mg]Br>O1CCCC1.[Cl-].N>[O:11]1[CH2:10][C:9]2([CH2:8][CH:7]3[CH:14]([CH:6]3[C:4](=[O:5])[CH3:16])[CH2:13]2)[CH2:12]1

Participants

5

Reactant 2

HCID 118161615HCID 118161615, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 118161656HCID 118161656, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 20976574Ammonia chlorideSolvent

Procedure

To an ice-cooled solution of N-methoxy-N-methylspiro[bicyclo[3.1.0]hexane-3,3′-oxetane]-6-carboxamide (0.30 g, 1.4 mmol) in tetrahydrofuran (15 mL) was added methylmagnesium bromide (1 mL, 3M in tetrahydrofuran) dropwise. After 1 h, the reaction mixture was diluted with saturated aqueous ammonia chloride solution (10 mL), and the resulting solution was extracted with ethyl acetate (3×20 mL). The collected organic was concentrated to provide product as a brown oil (220 mg, 93% yield).

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate (3×20 mL)
  2. concentrationThe collected organic was concentrated

Sources & evidence

ORD record
ord-63c90f9f03ef4b9eaef18128f2ea25ba
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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