(+)-1-(1-Naphthyl)ethylamine → HCID 58934736, compound

HRID 855083Notes

Reaction equation

HRID 855083 reaction equation
[CH2:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([OH:21])=[O:20])[CH:11]([C:15]([F:18])([F:17])[F:16])[O:12]2)=[CH:7][C:6]=1[Cl:22])[CH2:2][CH2:3][CH3:4].C1([C@H](N)C)C2C(=CC=CC=2)C=CC=1>>[CH2:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([OH:21])=[O:20])[C@H:11]([C:15]([F:16])([F:17])[F:18])[O:12]2)=[CH:7][C:6]=1[Cl:22])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 58934781HCID 58934781, compound

Product 1

HCID 58934736HCID 58934736, compound

Procedure

A racemic mixture of the compound prepared in Example 9a, Step 5 was chirally resolved using the same protocol as for Example 609e, Step 1, R-enantiomer was identified as peak 1 with retention time 5.38 min: ESHRMS m/z 333.0489 (M−H, C15H13ClF3O3 Calc'd 333.0500). 1HNMR (DMSO-d6/400 MHz), 13.13 (s, 1H), 7.79 (s, 1H), 7.56 (s, 1H), 7.00 (s, 1H), 5.89 (q, 1H, J=7.1 Hz), 2.62 (t, 2H, J=7.5 Hz), 1.50 (m, 2H), 1.30 (m, 2H), 0.860 (t, 3H, J=7.3 Hz). 19FNMR (d6-benzene; 6 eq of (R)-(+)-1-(1-naphthyl)ethylamine) d −77.82 (d, 3F, J=6.8 Hz, R-enantiomer), −77.78 (d, 3F, J=6.8 Hz, S-enantiomer).

Sources & evidence

ORD record
ord-4d720c7eaa9540989f4e87ebd604ec47
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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