Methanol → HCID 18511649, compound

HRID 1370539Notes

Reaction equation

HRID 1370539 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)=[CH:4][CH:3]=1.[ClH:21].[CH3:22][NH2:23].CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[ClH:21].[ClH:21].[CH3:22][NH:23][CH:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:15][CH2:16]1

Participants

7

Reactant 4

HCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 18511669HCID 18511669, compound

Product 1

HCID 18511649HCID 18511649, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 14.7 g (52.6 mmol) of the preceding ketoamine (22.2) in 150 ml of CH2Cl2 is treated with 3.5 g (52.6 mmol) of methylamine hydrochloride and then methanol is added until dissolution is complete. After stirring for 3 h at 25° C., the mixture is cooled on an ice bath and 14.5 g (68.5 mmol) of sodium triacetoxyborohydride are added portionwise and, finally, 3 ml of acetic acid are added dropwise. Stirring is continued overnight at 25° C. The reaction mixture is poured into ice and basified to pH 12-13. The base released is extracted in the usual way to give a greenish oil.

Workup

  1. temperaturethe mixture is cooled on an ice bath
  2. stirringStirring
  3. waitis continued overnight at 25° C
  4. additionThe reaction mixture is poured into ice and basified to pH 12-13
  5. extractionThe base released is extracted in the usual way
  6. customto give a greenish oil

Sources & evidence

ORD record
ord-249ba6bf9b3940c5a9c495d1ed9b19f0
Source dataset
uspto-grants-2003_06
Patent number
US06583159B1

Reaction notes

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