Water → HCID 86644156, compound

HRID 1523641Notes

Reaction equation

HRID 1523641 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[O:8][C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:6][C@H:5]1[CH:14]=O.[OH2:16].Cl.[NH2:18]O.C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:6][CH:5]1[CH:14]=[N:18][OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 86644155HCID 86644155, compound

Product 1

HCID 86644156HCID 86644156, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude (2R,3S)-3-(methoxymethyl)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde (31 g, 145 mmol) was dissolved in 1:1 methanol:water (600 mL), and hydroxylamine hydrochloride (10.1 g, 145 mmol) and Na2CO3 (7.67 g, 72.3 mmol) were added. The reaction was stirred at ambient temperature for 3 hours. The methanol was removed under reduced pressure and the remaining material was extracted with CH2Cl2, dried over sodium sulfate, filtered and concentrated to afford 3-(methoxymethyl)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde oxime (33.6 g, 147 mmol, 101% yield) which was taken forward without purification.

Workup

  1. customThe methanol was removed under reduced pressure
  2. extractionthe remaining material was extracted with CH2Cl2
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e0fc364bd33d4a568e32c3eab121f119
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

Loading…