Benzaldehyde, 4-octyl- → HCID 178442644, compound

HRID 898213Notes

Reaction equation

HRID 898213 reaction equation
[NH2:1][CH2:2][CH:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][P:5](C(OCC)OCC)(=[O:9])[O:6]CC.[CH2:23]([C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CO>[CH2:23]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH:1][CH2:2][CH:3]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:4][PH:5](=[O:9])[OH:6])=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 2734685Benzaldehyde, 4-octyl-HCID 14362832Ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate

Product 1

HCID 178442644HCID 178442644, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 69.2 mg (0.210 mmol) of ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate (Tetrahedron, 1989, 3787-3808) and 48.2 mg (0.221 mmol) of 4-octylbenzaldehyde in 1 mL of MeOH at rt was treated with 6.7 mg (0.105 mmol) of Na(CN)BH3. The resulting reaction mixture was stirred at rt for 16 hr. The reaction was quenched with 0.3 mL of 12 N HCl, then heated up to 60° C. for 5 hr. The mixture was cooled and concentrated. HPLC purification (LC-2) afforded 22 mg (26%) of the title compound. 1H NMR (500 MHz) (CD3OD) δ 0.88 (t, J=7.1, 3H), 1.26-1.30 (m, 10H), 1.58-1.61 (m, 2H), 2.01-2.17 (m, 2H), 2.62 (t, J=7.8, 2H), 3.20-3.23 (m, 1H),3.35-3.46 (m, 2H), 4.11 (s, 2H), 6.92 (d, J=535.4, 1H), 7.23-7.37 (m, 9H); LC-1: 3.31 min; ESI-MS 402 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with 0.3 mL of 12 N HCl
  3. temperatureheated up to 60° C. for 5 hr
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. customHPLC purification (LC-2)

Sources & evidence

ORD record
ord-ac18f86ffd9b427091b42427475c7bf7
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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