Sodium cyanoborohydride → HCID 66809062, compound

HRID 556155Notes

Reaction equation

HRID 556155 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[CH2:12][C:11](=O)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.CN.[C:25]([BH3-])#[N:26].[Na+]>C1COCC1.CO.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[CH2:12][CH:11]([NH:26][CH3:25])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 58950768HCID 58950768, compound

Product 1

HCID 66809062HCID 66809062, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the tetralone 30a in THF in methanol was added methylamine hydrochloride. After dissolution (10 min), sodium cyanoborohydride was added in a single portion. The resultant mixture was stirred at 50° C. for three hours. After cooling, the mixture was diluted with sodium bicarbonate solution and extracted with MTBE. The organic layer was evaporated to give the crude amine 32a (160 mg) as a mixture of four configurational isomers.

Workup

  1. additionwas added in a single portion
  2. temperatureAfter cooling
  3. extractionextracted with MTBE
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-6233025d4cb94bd4a25bdf2aec2a86d6
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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