Methanol → (1RS,5RS)-4-(4-chlorobenzyl)-1-methyl-6-oxa-bicyclo[3,2,0]heptane-5-carboxyamide

HRID 922743Notes

Reaction equation

HRID 922743 reaction equation
ClC1C=CC(CC2[C:13]3([C:14]#[N:15])C(C)(CO3)CC2)=CC=1.COC([C:23]1([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[CH2:27][CH2:26][C:25]([CH2:29]O)([CH3:28])[C:24]1=[O:31])=O.C[OH:41].[H-].[Na+]>O1CCCC1.O>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([CH2:32][CH:23]2[C:24]3([CH2:13][C:14]([NH2:15])=[O:41])[C:25]([CH3:28])([CH2:29][O:31]3)[CH2:26][CH2:27]2)=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 672540121-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl esterHCID 86718265(1RS,5RS)-4-(4-chlorobenzyl)-1-methyl-6-oxa-bicyclo[3,2,0]heptane-5-carbonitrile

Product 1

HCID 131734985(1RS,5RS)-4-(4-chlorobenzyl)-1-methyl-6-oxa-bicyclo[3,2,0]heptane-5-carboxyamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 7 ml of tetrahydrofuran, 703 mg of Compound 5-1 obtained in Production Example 9 of Example 1 was dissolved. To the solution thus obtained, 7 ml of methanol and 5 ml of 25% aqueous solution of sodium hydride were added, and the resulting mixture was refluxed in hot water bath of 80° C. for 5 hours. After the reaction, the solvent was distilled away, and the residue was then mixed with water.

Workup

  1. dissolutionwas dissolved
  2. customTo the solution thus obtained
  3. customAfter the reaction
  4. distillationthe solvent was distilled away
  5. additionthe residue was then mixed with water

Sources & evidence

ORD record
ord-4a8da9353554476d861acadc75d6fed8
Source dataset
uspto-grants-2016_03
Patent number
US09278966B2

Reaction notes

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