(+)-1-(1-Naphthyl)ethylamine → HCID 58934826, compound

HRID 855085Notes

Reaction equation

HRID 855085 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[O:8][CH:7]([C:18]([F:21])([F:20])[F:19])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2.C1([C@H](N)C)C2C(=CC=CC=2)C=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][CH2:13][C:14]([CH3:17])([CH3:15])[CH3:16])[O:8][C@H:7]([C:18]([F:21])([F:19])[F:20])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2

Participants

3

Reactant 2

HCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 58934760HCID 58934760, compound

Product 1

HCID 58934826HCID 58934826, compound

Procedure

A racemic mixture of the compound prepared in Example 9b, Step 3 was chirally resolved using the same protocol as for Example 609e, Step 1, S-enantiomer was identified as peak 2 with retention time 10.35 min: ESHRMS m/z 361.0848 (M−H, C17H17ClF3O3 Calc'd 361.0813). 1HNMR (DMSO-d6/400 MHz) 13.23 (brs, 1H, 7.80 (s, 1H), 7.55 (s, 1H), 7.01 (s, 1H), 5.89 (q, 1H, J=7.1 Hz), 3.30 (m, 2H), 2.56-2.60 (m, 2H), 1.31-1.37 (m, 2H), 0.91 (s, 9H). 19FNMR (d6-benzene; 6 eq of (R)-(+)-1-(1-naphthyl)ethylamine) d−77.80 (d, 3F, J=6.8 Hz, R-enantiomer), −77.77 (d, 3F, J=6.8 Hz, S-enantiomer).

Sources & evidence

ORD record
ord-60dc8e436ed043c688c4b70da701d117
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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