Formic Acid → methyl N-(decahydro-1-naphthalenyl)-N-formylglycine

HRID 621386Notes

Reaction equation

HRID 621386 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](O)=O.C(OC(=O)C)(=[O:19])C.[CH:24]([OH:26])=[O:25]>>[CH3:4][CH:3]([C:24]([OH:26])=[O:25])[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:19]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 70377605methyl N-(decahydro-1-naphthalenyl)glycine

Product 1

HCID 86742951methyl N-(decahydro-1-naphthalenyl)-N-formylglycineYield 89.4%

Conditions

Temperature
5 °C

Procedure

150 Parts of methyl N-(decahydro-1-naphthalenyl)glycine were added dropwise to 372 parts of formic acid while cooling (5° C.). Upon complete addition, 110 parts of acetic acid anhydride were added. The reaction mixture was stirred for 17 hours at room temperature. The whole was distilled in vacuo, yielding 142.8 parts (89.4%) of methyl N-(decahydro-1-naphthalenyl)-N-formylglycine as a residue (intermediate 6).

Workup

  1. additionwere added
  2. distillationThe whole was distilled in vacuo

Sources & evidence

ORD record
ord-3869677ef79f410b80d55d0f995af785
Source dataset
uspto-grants-1989_04
Patent number
US04824472

Reaction notes

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