1,4-Dioxane → HCID 14276851, compound

HRID 477738Notes

Reaction equation

HRID 477738 reaction equation
[CH2:1]([S:8][C:9]1[N:13]=[C:12]([NH:14][CH:15]=O)[N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[BH4-].[Na+]>C(O)(=O)C>[CH2:1]([S:8][C:9]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 4311764Sodium borohydrideHCID 14276850HCID 14276850, compound

Product 1

HCID 14276851HCID 14276851, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

The product of stage (a) (31 g) was mixed with dioxan (200 ml) and 96% sodium borohydride (19.6 g) at room temperature, and acetic acid (30 ml) was added with vigorous stirring. The mixture was stirred at 100° C. for 2 hours, after which the solvents were removed and the mixture was added carefully to water. The product was then extracted with ethyl acetate and chromatographed on silica gel to give 21.4 g of the desired product.

Workup

  1. customafter which the solvents were removed
  2. additionthe mixture was added carefully to water
  3. extractionThe product was then extracted with ethyl acetate
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-7a3fc55fe2f044f3907546ea45f96ebd
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

Loading…