1-Deoxy-1-(2-hydroxyethylamino)-D-glucitol → 1-(2-Hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

HRID 1450136Notes

Reaction equation

HRID 1450136 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][C@@H:6]([C@H:8]([C@@H:10]([C@@H:12]([CH2:14][OH:15])O)[OH:11])[OH:9])[OH:7].OCCNC[C@@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O>>[CH2:5]1[N:4]([CH2:3][CH2:2][OH:1])[CH:12]([CH2:14][OH:15])[CH:10]([OH:11])[CH:8]([OH:9])[CH:6]1[OH:7]

Participants

3

Reactant 2

HCID 200555691-Deoxy-1-(2-hydroxyethylamino)-D-glucitolHCID 53717314HCID 53717314, compound

Product 1

HCID 515771-(2-Hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triolYield 95%

Procedure

N-(2-hydroxyethyl)glucamine is microbially oxidized in substantial accordance with the teaching of Example 26, except N-(2-hydroxyethyl)glucamine is used in place of N-ethylglucamine and N-(2-hydroxyethyl)-1-deoxynojirimycin is obtained instead of N-ethyl-1-deoxynojirimycin. HPLC analysis after 24 hours indicates that 79% of the initial charge of N-(2-hydroxyethyl)glucamine has been converted to 6-(2-hydroxyethyl)amino-6-deoxy-α-L-sorbofuranose. After 48 hours, at least 90% of the initial charge has been converted. After 72 hours, the supernatant is separated from the cells and sterile filtered. The pH of an aliquot (10 mL) is adjusted to pH 9.0 with concentrated NH4OH, chilled in an ice bath, and 100 mg NaBH4 is added. After standing in the ice bath overnight, the samples are acetylated and assayed by gas chromatography mass spectroscopy (GC-MS). GC-MS indicates a 95% yield of N-(2-hydroxyethyl)-1-deoxynojirimycin from 6-(2-hydroxyethyl)amino-6-deoxy-α-L-sorbofuranose (chemical ionization mass spectroscopy of the acetylated product indicated the GC peak corresponding to the reduced, cyclized product has a parent peak mass of 418 (M+H) corresponding to the penta-acetylated N-2-hydroxyethyl-1-deoxynojirimycin.

Workup

  1. waitAfter 48 hours
  2. additionat least 90% of the initial charge
  3. waitAfter 72 hours
  4. customthe supernatant is separated from the cells and sterile filtered
  5. temperaturechilled in an ice bath
  6. addition100 mg NaBH4 is added
  7. customAfter standing in the ice bath overnight

Sources & evidence

ORD record
ord-0d4d70ec1aa2490580e02b432216555d
Source dataset
uspto-grants-1997_02
Patent number
US05602013

Reaction notes

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