Trimethylphosphine → HCID 86680028, compound

HRID 1915819Notes

Reaction equation

HRID 1915819 reaction equation
[N:1]([C:4]1([CH3:19])[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6][CH:5]1[OH:18])=[N+]=[N-].CP(C)C>C1COCC1.O>[NH2:1][C:4]1([CH3:19])[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:6][CH:5]1[OH:18]

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 86680026HCID 86680026, compound

Product 1

HCID 86680028HCID 86680028, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-azido-1-benzyl-5-methylazepan-4-ol (1.5 g, 5.76 mmol) in THF (12 mL) and water (4 mL) was added slowly a solution of trimethylphosphine (1 M in toluene, 28 mL, 28.9 mmol) and the reaction was stirred at 65° C. for 18 hr. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was dissolved in 1 M HCl (30 mL) and extracted with EtOAc (2×25 mL). The aqueous layer was basified to pH14 with aqueous 6 M NaOH and extracted with DCM (3×30 mL). The combined organic layers were passed through a phase separation cartridge concentrated under reduced pressure. Purification via silica gel column chromatography (1-10% 7 M NH3 in MeOH/DCM) gave 5-amino-1-benzyl-5-methylazepan-4-ol as a viscous yellow oil (1.2 g, 89%). 1H NMR (400 MHz, CDCl3) δ 7.34-7.20 (m, 5H), 3.60-3.52 (m, 2H), 3.50-3.46 (m, 2H), 2.80-2.79 (m, 1H), 2.70-2.45 (m, 4H), 2.15-1.95 (m, 1H), 1.79-1.72 (m, 2H), 1.49-1.40 (m, 2H), 1.19 (s, 3H).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 1 M HCl (30 mL)
  4. extractionextracted with EtOAc (2×25 mL)
  5. extractionextracted with DCM (3×30 mL)
  6. customThe combined organic layers were passed through a phase separation cartridge
  7. concentrationconcentrated under reduced pressure
  8. customPurification via silica gel column chromatography (1-10% 7 M NH3 in MeOH/DCM)

Sources & evidence

ORD record
ord-a7b33c9561534db8902a2a2850ce675f
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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