Sodium cyanoborohydride → HCID 24857670, compound

HRID 556147Notes

Reaction equation

HRID 556147 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][C:11](=O)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.CN.[C:23]([BH3-])#[N:24].[Na+]>C1COCC1.CO.CC(OC)(C)C>[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][CH:11]([NH:24][CH3:23])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 24857665HCID 24857665, compound

Product 1

HCID 24857670HCID 24857670, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ketone 5 (350 mg, 1.202 mmol) in THF (18 mL) and methanol (24 mL) was added methylamine hydrochloride (980 mg, 10 eq). After the solid dissolved, sodium cyanoborohydride (6.0 mL, 1 M in THF, 5 eq) was added in one portion. The mixture was heated in a 50° C. oil bath overnight before being quenched with aqueous sodium bicarbonate and extracted with MTBE. The combined organic layer was washed with brine and evaporated to give a brown-green oil. The oil was dissolved in MTBE and extracted into 10% aqueous hydrochloric acid. The aqueous layer was basicified with KOH and extracted with MTBE. The volatile components were removed in vacuo and the crude green oil was separated on silica gel to give the methylamine (0.20 g, 54%) as a pale-green oil.

Workup

  1. dissolutionAfter the solid dissolved
  2. custombefore being quenched with aqueous sodium bicarbonate
  3. extractionextracted with MTBE
  4. washThe combined organic layer was washed with brine
  5. customevaporated
  6. customto give a brown-green oil
  7. extractionextracted into 10% aqueous hydrochloric acid
  8. extractionextracted with MTBE
  9. customThe volatile components were removed in vacuo
  10. customthe crude green oil was separated on silica gel

Sources & evidence

ORD record
ord-8556594f510d4c0c9ed67d2e87d23ddf
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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