(-)-Mandelic acid → HCID 7316107, compound

HRID 2368960Notes

Reaction equation

HRID 2368960 reaction equation
[C:1]1([CH2:7][CH:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)[C@@H](C1C=CC=CC=1)O>>[C:1]1([CH2:7][C@@H:8]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 11914(-)-Mandelic acidHCID 1025541-Phenyl-2-(benzylamino)propane

Product 1

HCID 7316107HCID 7316107, compoundYield 86%

Procedure

A sample of 5.0 g (22.2 mmol) of racemic 1-phenyl-2-benzylaminopropane (38) was reacted with 3.4 g (22.2 mmol) of (R)-(−)-mandelic acid to give 2.15 g (86% based on enantiomeric abundance) of the free amine after workup. 1H NMR (CDCl3) δ 1.11 (d, 3H, J=6.0 Hz), 2.62-2.84 (m, 2H), 2.92-2.99 (m, 1H), 3.81 (dd, 2H, J=13.2, 34.5 Hz), 7.14-7.29 (m, 5H); MS (APCI+) m/z (rel): 226 (100); [α]D=+18.2° (c=0.85 MeOH).

Sources & evidence

ORD record
ord-d272ee0ac3da4342947c8c675b58122f
Source dataset
uspto-grants-2014_04
Patent number
US08703826B2

Reaction notes

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