Ethylamine → HCID 58954861, compound

HRID 333275Notes

Reaction equation

HRID 333275 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[C:17](=O)[O:16][CH2:15][CH:14]2[CH2:13][CH2:12][CH2:11][CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:19]([NH2:21])[CH3:20]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:17][NH:21][CH2:19][CH3:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:15][OH:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 67420038HCID 67420038, compound

Product 1

HCID 58954861HCID 58954861, compound

Procedure

The title compound was prepared from racemic 7a-(3,4-dichlorophenyl)hexahydroisobenzofuran-1(3H)-one and ethylamine according to General Procedures AA, followed by General Procedure E. The racemic aminol was separated using a chiral column (Chiracel OD column; 95:5:0.1 hexanes:IPA:DEA, λ=254 nm, 1 mL/min) to give the fast moving enantiomer 169 E1 (Rt=7.5 min) and the slow moving enantiomer 169 E2 (Rt=9.7 min). LCMS Rt=7.88 min, m/z=316 (M+1). 1H NMR (CDCl3, δ): 7.4 (m, 2H), 7.17 (dd, J=2.4, 8.5 Hz, 1H), 3.7 (m, 2H), 3.10 (d, J=12.3 Hz, 1H), 2.71 (d, J=12.3 Hz, 1H), 2.6 (m, 2H), 2.3 (m, 1H), 1.9-1.3 (m, 8H), 1.04 (t, J=7.2 Hz, 3H). 13C NMR (CDCl3, δ, mult): 146.5(0), 133.1(0), 130.8(1), 130.0(0), 128.5(1), 125.7(1), 63.2(2), 53.6(br, 2), 45.4(0), 43.9(2), 41.9(1), 39.8(br, 2), 26.1(2), 24.8(2), 22.0(2), 14.5(3).

Workup

  1. customThe racemic aminol was separated
  2. customto give the

Sources & evidence

ORD record
ord-f77a1ab048564d92a691372d7ae98281
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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