Ammonium Hydroxide → HCID 59104144, compound

HRID 899384Notes

Reaction equation

HRID 899384 reaction equation
C([N:4](CC=C)[C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1)[CH3:6])C=C.[NH4+].[OH-]>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:4][C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1)[CH3:6]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 59104136HCID 59104136, compound

Product 1

HCID 59104144HCID 59104144, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.63 g (0.54 mmol) Pd(PPh3)4 and 25.3 g (162 mmol) NDMBA was combined and placed under N2. Thereafter, a solution of 7.0 g (27 mmol) (R)-2-[4-(1-diallylamino-ethyl)-phenyl]-propan-2-ol in 140 ml CH2Cl2 was added. The resulting mixture was then refluxed under N2 for 2 hours. The crude reaction mixture was then loaded onto coarse silica gel. Chromatography on silica gel using 7.5% MeOH/CH2Cl2 followed by 2% NH4OH/ 10% MeOH/CH2Cl2 yielded 4.5 g (93%) of the desired product.

Workup

  1. temperatureThe resulting mixture was then refluxed under N2 for 2 hours
  2. customThe crude reaction mixture

Sources & evidence

ORD record
ord-9d3c3d5b078647cba7a94acdb7c66811
Source dataset
uspto-grants-2008_04
Patent number
US07354941B2

Reaction notes

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