Triphenylphosphine → HCID 59201507, compound

HRID 451723Notes

Reaction equation

HRID 451723 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C@:7]([C@@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]1)([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:8][CH2:9][CH3:10])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH2:4][CH2:5][O:6][C@:7]([C@@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:19]1)([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 59201594HCID 59201594, compound

Product 1

HCID 59201507HCID 59201507, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of (R)-tert-butyl 3-((R)-1-(2-azidoethoxy)-1-(3-chlorophenyl)butyl)piperidine-1-carboxylate (790 mg, 1.81 mmol) in the mixture of THF/H2O (20:1, 10.5 mL) was added PPh3 (1.9 g, 7.25 mmol). The reaction mixture was stirred at rt overnight. The solvent was removed under reduced pressure to the residue, which was purified by column chromatography on silica gel to afford (R)-tert-butyl 3-((R)-1-(2-aminoethoxy)-1-(3-chlorophenyl)butyl)piperidine-1-carboxylate (410 mg, 55%). 1HNMR (CDCl3, 400 MHz) δ 7.31 (s, 1H), 7.24 (m, 2H), 7.15 (m, 1H), 4.31-3.52 (m, 3H), 3.27 (m, 2H), 2.93 (m, 1H), 2.41-2.22 (m, 3H), 2.15-1.95 (m, 3H), 1.85 (m, 4H), 1.57 (m, 1H), 1.44 (s, 9H), 1.38-1.10 (m, 2H), 0.95 (t, 31).

Workup

  1. customThe solvent was removed under reduced pressure to the residue, which
  2. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a1c01e015de74e2187d9efcd32c73037
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

Loading…