Acetic Acid → HCID 15703785, compound

HRID 1534374Notes

Reaction equation

HRID 1534374 reaction equation
[OH:1][C:2]1[C:13]2[C:12](=[O:14])[O:11][CH2:10][C:9]3[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([O:19][CH3:20])[C:8]=3[O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22](=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25].C(O)(=O)C.C([BH3-])#N.[Na+]>O1CCCC1>[OH:1][C:2]1[C:13]2[C:12](=[O:14])[O:11][CH2:10][C:9]3[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([O:19][CH3:20])[C:8]=3[O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH:22]([OH:27])[CH2:23][CH:24]([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 15703788HCID 15703788, compound

Product 1

HCID 15703785HCID 15703785, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.2 g (5.9 mmol) of the compound from Example 109 are dissolved in 40 ml of tetrahydrofuran, and 7 ml of glacial acetic acid and 0.96 g (15 mmol) of sodium cyanoborohydride are added. After 14 h at room temperature, the mixture is concentrated in vacuo, the residue is taken up in dichloromethane, and the solution is washed with sodium hydrogen carbonate solution and water, dried over magnesium sulphate and concentrated in vacuo. Purification is carried out by column chromatography on silica gel using dichloromethane/methanol 150/1 as the eluent.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. washthe solution is washed with sodium hydrogen carbonate solution and water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-d893a25856ea4b989cdbe827b1c37d1a
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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