Dichloromethane methanol ammonium hydroxide → HCID 10215440, compound

HRID 1454348Notes

Reaction equation

HRID 1454348 reaction equation
[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:21][CH2:20][C:19]([C:23]([O:25]C)=[O:24])(F)[CH2:18]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(Cl)Cl.C[OH:31].[NH4+].[OH-]>>[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:21][CH2:20][C:19]([C:23]([OH:25])=[O:24])([OH:31])[CH2:18]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 131727247HCID 131727247, compound

Product 1

HCID 10215440HCID 10215440, compound

Procedure

The title compound was prepared using an analogous procedure described in EXAMPLE 34, Step E substituting (R/S)-1-(4-nonylphenyl)methyl-3-hydroxypyrrolidin-3-yl carboxylic acid, methyl ester (from Step A) for (R/S)-1-(4-nonylphenyl)methyl-3-fluoropyrrolidin-3-yl carboxylic acid, methyl ester: RF: 0.15 (90:10:1 v/v/v CH2Cl2/MeOH/NH4OH); 1H-NMR (500 MHz, CD3OD) δ 0.89 (t, J=6.9, 3H), 1.28-1.33 (m, 12H), 1.60-1.63 (m, 2H), 2.10 (m, 1H), 2.49 (m, 1H), 2.64 (t, J=7.7, 2H), 3.25 (m, 1H), 3.49-3.62 (m, 3H), 4.38 (ABq, J=13.0, 2H), 7.28 (d, J=7.8, 2H), 7.42 (d, J=7.8, 2H); ESI-MS 348 (M+H); LC-1: 3.0 min.

Workup

  1. custom3.0 min.

Sources & evidence

ORD record
ord-b787cf6d757e47128b62b51db0b2b416
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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