Methanol → HCID 86746963, compound

HRID 1587755Notes

Reaction equation

HRID 1587755 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:19][C@H:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][C:11]=3[CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:7]([C:28]#[N:29])[CH2:6]1)=O.CO.[BH4-].[Na+].C(OCC)(=O)C>O1CCCC1.N1C=CC=CC=1>[C:28]([N:7]1[C@H:8]2[C@@H:18]([C:17]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:20]=3[C:10]([CH2:9]2)=[C:11]([CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[NH:12]4)[CH2:19][C@@H:5]([CH2:3][OH:2])[CH2:6]1)#[N:29]

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86746962HCID 86746962, compound

Product 1

HCID 86746963HCID 86746963, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.95 g of 6-cyano-2-morpholinomethyl-8beta-ergoline-carboxylic acid methyl ester (10 mmol) is dissolved in 250 ml of tetrahydrofuran and 250 ml of methanol and altogether 4 g of sodium borohydride is added in four portions at room temperature. After two hours of reaction time, the organic phases are mixed with ice and common salt, shaken with ethyl acetate, combined and dried and concentrated by evaporation. After crystallization from the ethyl acetate, 3.26 g (89% of theory) is obtained, [α]D =+46° (0.5% in pyridine).

Workup

  1. customAfter two hours of reaction time
  2. additionthe organic phases are mixed with ice and common salt
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customAfter crystallization from the ethyl acetate
  6. custom3.26 g (89% of theory) is obtained

Sources & evidence

ORD record
ord-523dd107184640079f948335b6e270de
Source dataset
uspto-grants-1993_06
Patent number
US05219862

Reaction notes

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