Sodium cyanoborohydride → HCID 66809019, compound

HRID 556158Notes

Reaction equation

HRID 556158 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][C:10]2=O)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.CN.[C:23]([BH3-])#[N:24].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH:10]2[NH:24][CH3:23])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 58950766HCID 58950766, compound

Product 1

HCID 66809019HCID 66809019, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetralone 35 (400mg, 1.374 mmol) in THF (10 mL) and methanol (15mL) was added methylamine hydrochloride (1.12 g, 10 eq). The resultant mixture was stirred at 50° C. After dissolution (10 min), sodium cyanoborohydride (6.9 mL, 1M in THF, 5 eq) was added in a single portion. After 20 hours, the organic layer was evaporated, filtered through silica and an aminopropyl cartridge. The crude oil was then diluted with sodium bicarbonate solution and extracted with MTBE to give the amine (280 mg, 66%) as a mixture of four stereoisomers (1:1:1:1).

Workup

  1. additionwas added in a single portion
  2. customthe organic layer was evaporated
  3. filtrationfiltered through silica
  4. additionThe crude oil was then diluted with sodium bicarbonate solution
  5. extractionextracted with MTBE

Sources & evidence

ORD record
ord-cdd6fcdf49fa41bbbc316c47f01da079
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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