Oxalic Acid → Oxalic acid--2-oxa-6-azaspiro(3.3)heptane (1/1)

HRID 1850314Notes

Reaction equation

HRID 1850314 reaction equation
C1(C)C=CC(S([N:10]2[CH2:16][C:12]3([CH2:15][O:14][CH2:13]3)[CH2:11]2)(=O)=O)=CC=1.[Mg].[C:19]([OH:24])(=[O:23])[C:20]([OH:22])=[O:21]>CO>[C:19]([OH:24])(=[O:23])[C:20]([OH:22])=[O:21].[CH2:13]1[C:12]2([CH2:16][NH:10][CH2:11]2)[CH2:15][O:14]1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 5462224MagnesiumHCID 233198916-Tosyl-2-oxa-6-azaspiro[3.3]heptane

Product 1

HCID 53308464Oxalic acid--2-oxa-6-azaspiro(3.3)heptane (1/1)Yield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-(toluene-4-sulfonyl)-2-oxa-6-aza-spiro[3.3]heptane (128) (1.27 g, 5 mmol) in MeOH (10 mL) was added magnesium chips. The mixture was reacted using ultrasound at RT for 20 mins. Oxalic acid was added and the mixture was stirred for 15 min, then concentrated to give oxalate salt (129) (1.06 g, 3.68 mmol, yield: 73.6%).

Workup

  1. customThe mixture was reacted
  2. customat RT
  3. customfor 20 mins
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-db348e85becf4438bb8d2d39fa26cb9b
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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