Ammonium Chloride → HCID 86746961, compound

HRID 1655088Notes

Reaction equation

HRID 1655088 reaction equation
[BH4-].[Na+].[CH2:3]([N:9]1[C:13]([C@@H:14]([OH:37])[C@@H:15]([C:25](N2[C@H](C(C)C)CCOC2=O)=[O:26])[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:12][N:11]=[CH:10]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl-].[NH4+]>CO>[CH2:3]([N:9]1[C:13]([C@@H:14]([OH:37])[C@H:15]([CH2:25][OH:26])[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:12][N:11]=[CH:10]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86746959HCID 86746959, compound

Product 1

HCID 86746961HCID 86746961, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (4×36 mg, 3.8 mmol) was added in batches at 30 minute intervals to a solution of the product of step (v) in methanol (4 ml) at 0° C. with stirring under argon. After stirring for a further 30 minutes, a saturated aqueous solution of ammonium chloride (5 ml) was added slowly. The mixture was extracted with ethyl acetate (3×10 ml) and the combined extracts dried (MgSO4), filtered and concentrated by evaporation. The residue was purified by column chromatography, eluting with 10% methanol/dichloromethane (v/v), to give methyl (7S,4Z)-7-[(S)-(1-hexylimidazol-5-yl)hydroxymethyl]-8-hydroxyoct-4-enoate (200 mg, 60% yield) as an oil;

Workup

  1. stirringAfter stirring for a further 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate (3×10 ml)
  3. dry with materialthe combined extracts dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with 10% methanol/dichloromethane (v/v)

Sources & evidence

ORD record
ord-f20077c794304140b326c9f7bd4ea7e7
Source dataset
uspto-grants-1995_04
Patent number
US05410064

Reaction notes

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