2-Methyl-5-phenylpentan-2-amine → Ethyl 3-(3-{(1S)-2-[(1,1-dimethyl-4-phenylbutyl)amino]-1-hydroxyethyl}-4,5-difluorophenyl)pentanoate

HRID 602048Notes

Reaction equation

HRID 602048 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:19][CH3:20])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[C:6]([C@H:9]2[CH2:11][O:10]2)[C:7]=1[F:8].[CH3:21][C:22]([NH2:33])([CH3:32])[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C>[CH3:32][C:22]([NH:33][CH2:11][C@H:9]([C:6]1[CH:5]=[C:4]([CH:12]([CH2:19][CH3:20])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:3]=[C:2]([F:1])[C:7]=1[F:8])[OH:10])([CH3:21])[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 122500142-Methyl-5-phenylpentan-2-amineHCID 57470583Ethyl 3-{3,4-difluoro-5-[(2S)-2-oxiranyl]phenyl}pentanoate

Product 1

HCID 68792304Ethyl 3-(3-{(1S)-2-[(1,1-dimethyl-4-phenylbutyl)amino]-1-hydroxyethyl}-4,5-difluorophenyl)pentanoateYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-{3,4-difluoro-5-[(2S)-2-oxiranyl]phenyl}pentanoate (8.56 g, 0.0301 mol) and (1,1-dimethyl-4-phenylbutyl)amine (5.39 g, 0.0304 mol) in ethanol (50 mL) was heated at 70° C. overnight. The reaction was concentrated and purified by column chromatography (0-40% ethyl acetate:hexane) yield the desired product (9.53 g, 69%). MS (m/z): 434.2 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography (0-40% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-6002ccbc47b0474fa79030fe86b6a342
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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