Methanol → HCID 178483648, compound

HRID 2118241Notes

Reaction equation

HRID 2118241 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:22])[CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][O:18]C(=O)C)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CO>O1CCOCC1>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([CH2:17][OH:18])[CH2:15][CH2:16]1)[CH3:22])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 178476334HCID 178476334, compound

Product 1

HCID 178483648HCID 178483648, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
15 °C

Procedure

To a cooled (˜15° C.) and stirred solution of 18 g (57.4 mmol) of trans-acetic acid 4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexylmethyl ester in 135 ml of dioxane was added 63.2 mL (63.2mmol, 1.1 eq) of aqueous 1 M NaOH within 5 min. The reaction was homogenised with 13 mL of MeOH and 28.7 mL (28.7 mmol, 0.5 eq) of aqueous 1 M NaOH after 3 h, then stirred for additional 1.5 h. The reaction was evaporated to remove the dioxane, partitioned between Et2O (×3)/H2O, dried over Na2SO4 and evaporated to yield 17.13 g (quantitative) of trans-[2-(4-hydroxymethyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester, MS: 272 (MH+).

Workup

  1. customThe reaction was evaporated
  2. customto remove the dioxane
  3. custompartitioned between Et2O (×3)/H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-5649a8dc450e4883826fe0341b039556
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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