Benzaldehyde, 4-octyl- → HCID 178442645, compound

HRID 898212Notes

Reaction equation

HRID 898212 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5](C(OCC)OCC)(=[O:9])[O:6]CC.[CH2:17]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CO>[CH2:17]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:1][CH2:2][CH2:3][CH2:4][PH:5](=[O:9])[OH:6])=[CH:27][CH:26]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 2734685Benzaldehyde, 4-octyl-HCID 10422382Phosphinic acid, (3-aminopropyl)(diethoxymethyl)-, ethyl ester

Product 1

HCID 178442645HCID 178442645, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 98.5 mg (0.389 mmol) of ethyl 3-aminopropyl (diethoxymethyl)phosphinate (from Step B) and 84.9 mg (0.389 mmol) of 4-octylbenzaldehyde in 1 mL of MeOH at rt was treated with 12.2 mg (0.194 mmol) Na(CN)BH3. The resulting reaction mixture was stirred at rt for 16 hr. The reaction was quenched with 0.5 mL of 12 N HCl, then heated up to 80° C. for 1 hr. The mixture was cooled and concentrated. HPLC purification (LC-2) afforded 60 mg (47%) of the title compound: 1H NMR (500 MHz, CD3OD) δ 0.88 (t, J=7.1, 3H), 1.25-1.33 (m, 10H), 1.59-1.66 (m, 4H), 1.90-1.96 (m, 2H), 2.63 (t, J=7.7, 2H), 3.09 (t, J=6.9, 2H), 4.12 (s, 2H), 7.03 (d, J=505.6, 1H), 7.27 (d, J=8.0, 2H), 7.38 (d, J=8.0, 2H); LC-1: 3.02 min; ESI-MS 326 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with 0.5 mL of 12 N HCl
  3. temperatureheated up to 80° C. for 1 hr
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. customHPLC purification (LC-2)

Sources & evidence

ORD record
ord-430a0edb506540d7a71620ba4488423a
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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