Water → (1R,2R)-N1,N2-Bis(2-(diphenylphosphino)benzyl)cyclohexane-1,2-diamine

HRID 857831

Reaktionsgleichung

Reaktionsgleichung von HRID 857831
[BH4-].[Na+].[C:3]1([P:9]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:10]2[CH:44]=[CH:43][CH:42]=[CH:41][C:11]=2[CH:12]=[N:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[N:20]=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[P:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O>CO>[C:35]1([P:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][NH:20][C@@H:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C@H:14]2[NH:13][CH2:12][C:11]2[CH:41]=[CH:42][CH:43]=[CH:44][C:10]=2[P:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 11285891trans-N,N'-Bis(2-diphenylphosphanylbenzylidene)cyclohexane-1,2-diamine

Produkt 1

HCID 10909155(1R,2R)-N1,N2-Bis(2-(diphenylphosphino)benzyl)cyclohexane-1,2-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.14 g (30 mmol) of sodium borohydride are added a little at a time to a solution of 3.30 g (5.0 mmol) of trans-N,N′-bis(2-diphenylphosphanylbenzylidene)cyclohexane-1,2-diamine in 60 ml of methanol. The solution is refluxed for 24 hours and, after cooling to room temperature, admixed with 20 ml of water. The organic phase is extracted with 3×50 ml of dichloromethane and the combined organic phases are washed with 2×30 ml of 10% ammonium chloride solution and 30 ml of water. After drying over magnesium sulfate, the solvent is removed under reduced pressure and the residue is recrystallized from 30 ml of ethanol. The product precipitates in the form of light-yellow crystals in a yield of 2.68 g (4.0 mmol, 80%). 1H-NMR (400 MHz, CDCl3): δ=7.65–6.92 (m, 28 H, aromat. H), 4.11, 3.98 (2×d, J=13.4 Hz, 4 H, Ar—CH2), 2.21 (m, 2H, NCH), 1.63–1.27 (m, 8H, (CH2)4) ppm.

Aufarbeitung

  1. temperatureThe solution is refluxed for 24 hours
  2. extractionThe organic phase is extracted with 3×50 ml of dichloromethane
  3. washthe combined organic phases are washed with 2×30 ml of 10% ammonium chloride solution and 30 ml of water
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customthe residue is recrystallized from 30 ml of ethanol
  7. customThe product precipitates in the form of light-yellow crystals in a yield of 2.68 g (4.0 mmol, 80%)

Quellen und Nachweise

ORD-Eintrag
ord-47d6d6e38bc5420198343a106859ca55
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148174B2

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