Sodium Hydroxide → HCID 178484118, compound

HRID 967170Notes

Reaction equation

HRID 967170 reaction equation
CO[C:3]([C@H:5]1[CH2:10][CH2:9][C@@H:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16]CC2C=CC=CC=2)[CH2:7][CH2:6]1)=O.[OH-].[Na+].[CH3:26][NH-:27].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:34]([O:38][C:39]([O:41]C(OC(C)(C)C)=O)=O)([CH3:37])([CH3:36])[CH3:35]>O.O1CCOCC1>[C:34]([O:38][C:39](=[O:41])[N:27]([CH2:3][C@H:5]1[CH2:6][CH2:7][C@@H:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[CH2:9][CH2:10]1)[CH3:26])([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 21226445Aluminium lithium hydrideHCID 21952893MethylamideHCID 178501286HCID 178501286, compound

Product 1

HCID 178484118HCID 178484118, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In analogy to the sequence described in examples 15.6, 15.7, 15.8, 15.9 and 15.10, cis-4-(4-benzyloxy-butoxy)-cyclohexanecarboxylic acid methyl ester (example 15.5) was hydrolysed with sodium hydroxide in water/dioxane, then, the acid formed was converted into its N-methyl-amide, which was reduced with lithium aluminium hydride, treated with di-tert-butyl-dicarbonate and hydrogenated giving cis-[4-(4-hydroxy-butoxy)-cyclohexyl-methyl]-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS: 316 (MH+).

Workup

  1. customthe acid formed

Sources & evidence

ORD record
ord-4cd18c773b4b4056979089c7cacab1f6
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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