Triphenylphosphine → HCID 58968716, compound

HRID 2075093Notes

Reaction equation

HRID 2075093 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1([O:26][CH3:27])[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[Br:28]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:28][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1([O:26][CH3:27])[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 58968674HCID 58968674, compound

Product 1

HCID 58968716HCID 58968716, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-(hydroxymethyl)-4-(trifluoromethyl)phenyl)-4-methoxypiperidine-1-carboxylate (410 mg, 1.05 mmol) in methylene chloride (7 mL) were added N-bromosuccinimide (342 mg; 1.92 mmol) and triphenylphosphine (516 mg; 1.96 mmol). The reaction was stirred at room temperature for 1 hour. The reaction was then purified over 40 g RediSep column (Teledyne Isco Inc. Lincoln Nebr.) (eluted with 5-30% ethyl acetate in heptane) to give 433 mg (90% yield) of a colorless oil. MS (ES+). Calc: 452.3 (81Br), Found: 407.2 (M(81Br)—HCO2−). 1H NMR (400 MHz, CDCl3) δ ppm 7.82 (d, J=1.66 Hz, 1H), 7.52 (dd, J=8.30, 1.66 Hz, 1H), 7.34, (d, J=8.30 Hz, 1H), 5.08 (s, 2H), 4.04 (d, J=12.86 Hz, 2H), 3.21 (t, J=12.86, 13.28 Hz, 2H), 3.02 (s, 3H), 2.26 (d, J=14.11 Hz, 2H), 1.86 (t, J=12.86, 14.11 Hz, 2H), 1.48 (s, 9H).

Workup

  1. customThe reaction was then purified over 40 g RediSep column (Teledyne Isco Inc. Lincoln Nebr.) (eluted with 5-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-967c51cd982e467996a6ec16a8dbfe90
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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