Sodium borohydride → HCID 11369630, compound

HRID 2059072Notes

Reaction equation

HRID 2059072 reaction equation
[CH2:1]([N:4]1[C@H:18]2[C@@H:8]([C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:19]=3[C:16]([CH2:17]2)=[CH:15][NH:14]4)[CH2:7][C@@H:6]([C:20](OC)=[O:21])[CH2:5]1)[CH2:2][CH3:3].[BH4-].[Na+]>CO.O>[CH2:1]([N:4]1[C@H:18]2[C@@H:8]([C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:19]=3[C:16]([CH2:17]2)=[CH:15][NH:14]4)[CH2:7][C@@H:6]([CH2:20][OH:21])[CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 13345543HCID 13345543, compound

Product 1

HCID 11369630HCID 11369630, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

10 grams of 6-n-propyl-8β-methoxycarbonylergoline were added to a mixture of 10 g of sodium borohydride in 125 ml of methanol. The reaction mixture was refluxed for about 2 hrs; then a second 5 g batch of sodium borohydride was added. The reaction mixture was cooled after 5 hrs, diluted with water, and the precipitate was filtered to give 7.5 g of 6-n-propyl-8β-hydroxymethylergoline melting at about 166°-168° C. A solution of 15 g of 4-toluenesulfonyl chloride in 100 ml of pyridine was added slowly to a cooled solution of 7.5 g of 6-n-propyl-8β-hydroxymethylergoline in 300 ml of pyridine. The mixture was stirred for 7 hrs whereafter it was poured over iced water and the precipitate was filtered to give 9 g of 6-n-propyl-8β-toxyloxymethylergoline melting at 147°-150° C.

Workup

  1. temperatureThe reaction mixture was refluxed for about 2 hrs
  2. temperatureThe reaction mixture was cooled after 5 hrs
  3. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-a58082bc0e1340e4a5cb479645030216
Source dataset
uspto-grants-1982_03
Patent number
US04321381

Reaction notes

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