Methanol → HCID 178483648, compound

HRID 1063641Notes

Reaction equation

HRID 1063641 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 within 5 min 63.2 mL (63.2 mmol, 1.1 eq) of aqueous 1M NaOH. The reaction was homogenised with 13 mL of MeOH and 28.7 mL (28.7 mmol, 0.5 eq) of aqueous 1M 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-c25acae08a0b4da390f4e395fbf7da80
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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