Water → methyl N-(decahydro-1-naphthalenyl)-N-formylglycine

HRID 621384Notes

Reaction equation

HRID 621384 reaction equation
[CH3:1][N:2]([CH:7]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9][CH2:8]1)[CH2:3][C:4]([OH:6])=[O:5].[CH3:17]C1C=CC=CC=1.[OH2:24]>C(O)=O>[CH3:17][CH:3]([C:4]([OH:6])=[O:5])[N:2]([CH:7]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9][CH2:8]1)[CH:1]=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 1140TolueneHCID 70377605methyl N-(decahydro-1-naphthalenyl)glycine

Product 1

HCID 86742951methyl N-(decahydro-1-naphthalenyl)-N-formylglycineYield 71.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

A mixture of 82.2 parts of methyl N-(decahydro-1-naphthalenyl)glycine, 36 parts of formic acid and 360 parts of methylbenzene was stirred for 4 hours at reflux temperature, using a water separator (another portion of 36 parts of formic acid was added each hour). After cooling, the separated organic layer was washed with a formic acid solution 20% and a sodium hydrogen carbonate solution, dried, filtered and evaporated, yielding 66 parts (71.3%) of methyl N-(decahydro-1-naphthalenyl)-N-formylglycine as a residue (intermediate 2).

Workup

  1. temperatureat reflux temperature
  2. additionwas added each hour)
  3. temperatureAfter cooling
  4. washthe separated organic layer was washed with a formic acid solution 20%
  5. dry with materiala sodium hydrogen carbonate solution, dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-607bbda4b0284d318211ca172aa2c63c
Source dataset
uspto-grants-1989_04
Patent number
US04824472

Reaction notes

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