Carbon tetrabromide → N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(bromomethyl)phenyl]-N-propylmethanesulfonamide

HRID 899456Notes

Reaction equation

HRID 899456 reaction equation
C[CH2:2][S:3]([N:6]([C:10]1[CH:15]=[C:14]([CH2:16]O)[CH:13]=[C:12]([CH2:18][O:19][CH2:20][C:21]([NH2:30])([CH3:29])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:11]=1)[CH2:7][CH2:8][CH3:9])(=[O:5])=[O:4].C(Br)(Br)(Br)[Br:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[NH2:30][C:21]([CH3:29])([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][O:19][CH2:18][C:12]1[CH:11]=[C:10]([N:6]([CH2:7][CH2:8][CH3:9])[S:3]([CH3:2])(=[O:5])=[O:4])[CH:15]=[C:14]([CH2:16][Br:32])[CH:13]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67318200methyl N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(hydroxymethyl)phenyl]-N-propylmethanesulfonamide

Product 1

HCID 67319075N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(bromomethyl)phenyl]-N-propylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(hydroxymethyl)phenyl]-N-propylmethanesulfonamide (140 mg, 0.269 mmol) in dichloromethane (2.5 mL) were added carbon tetrabromide (116 mg, 0.350 mmol) and triphenylphosphine (85.0 mg, 0.323 mmol). After 15 h, the reaction mixture was concentrated in vacuo and purified by flash chromatography (silica, 0-35% EtOAc/hexanes) to provide N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(bromomethyl)phenyl]-N-propylmethanesulfonamide as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.34 (s, 1H), 7.31 (s, 1H),), 7.30-7.20 (m, 4H), 7.18-7.14 (m, 2H), 4.60-4.50 (m, 3H), 4.49 (s, 2H), 3.64 (t, J=7.2 Hz, 2H), 3.55 (A of AB, d, J=8.7 Hz, 1H), 3.45 (B of AB, d, J=8.7 Hz, 1H), 3.14 (A of AB, d, J=13.3 Hz, 1H), 2.94 (B of AB, d, J=13.3 Hz, 1H), 2.88 (s, 3H), 1.56-1.47 (m, 2H), 1.46 (s, 9H), 1.27 (s, 3H), 0.91 (t, J=7.4 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica, 0-35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a61e99680eb54a3288aded807b2d79b7
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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