Triphenylphosphine → 2-Aminocycloheptan-1-ol

HRID 1848019Notes

Reaction equation

HRID 1848019 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[OH:11])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH:4]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[OH:11]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 145662602-Azidocycloheptan-1-ol

Product 1

HCID 128869132-Aminocycloheptan-1-olYield 66.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of (±)-2-azidocycloheptanol (190 mg, 1.2 mmol) in THF (1 mL) and H2O (100 μL) was added PPh3 (321 mg, 1.2 mmol). The mixture was stirred at rt for 15 h, then concentrated under reduced pressure. The residue was purified via silica gel flash chromatography eluting with 100:15:1, CH2Cl2:MeOH:TEA to afford (±)-2-aminocycloheptanol (103 mg, 50%) as a white solid. LCMS (ELSD) (ESI) m/z 130 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified via silica gel flash chromatography
  3. washeluting with 100:15:1, CH2Cl2

Sources & evidence

ORD record
ord-6ad0c534dc124358877ec05837199d7a
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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