Sodium borohydride → HCID 70545904, compound

HRID 2059073Notes

Reaction equation

HRID 2059073 reaction equation
[CH: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)([CH3:3])[CH3:2].[BH4-].[Na+]>CO.O>[CH: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)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 14380966HCID 14380966, compound

Product 1

HCID 70545904HCID 70545904, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

8 grams of 6-isopropyl-8β-methoxycarbonylergoline was added to a mixture of 8 g of sodium borohydride in 200 ml of methanol. The reaction mixture was heated under reflux for 2 hrs; then a second 2 g batch of sodium borohydride was added. The mixture was cooled after 3 hrs, diluted with water, and the precipitate was filtered to give 6.5 g of 6-isopropyl-8β-hydroxymethylergoline, m.p. 192°-194° C., after crystallization from methanol. A solution of 13 g of 4-toluenesulfonyl chloride in 87 ml of pyridine was added slowly to a cooled solution of 6.5 g of 6-isopropyl-8β-hydroxymethylergoline in 250 ml of pyridine. After 15 hrs the mixture was poured over iced water and the precipitate was filtered to give 7.4 g of 6-isopropyl-8β-toxyloxymethylergoline melting at 180°-184° C. after crystallization from acetone.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. temperatureThe mixture was cooled after 3 hrs
  4. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-5e5a3e959a2c4ce5a9f7dd48dc137361
Source dataset
uspto-grants-1982_03
Patent number
US04321381

Reaction notes

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