(+)-1-(1-Naphthyl)ethylamine → HCID 58934679, compound

HRID 855088Notes

Reaction equation

HRID 855088 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:22]([OH:24])=[O:23])[CH:14]([C:18]([F:21])([F:20])[F:19])[O:15]2)=[CH:10][C:9]=1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([C@H](N)C)C2C(=CC=CC=2)C=CC=1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:22]([OH:24])=[O:23])[C@@H:14]([C:18]([F:19])([F:20])[F:21])[O:15]2)=[CH:10][C:9]=1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 58935058HCID 58935058, compound

Product 1

HCID 58934679HCID 58934679, compound

Procedure

A racemic mixture of the compound prepared in Example 42a, Step 2 was chirally resolved using the same protocol as for Example 609e, Step 1, identified as peak 2 with retention time 10.00 min. ESHRMS m/z 347.0894 (M−H, C19H14F3O3 Calc'd 347.0890). 1HNMR (DMSO-d6/400 MHz) 13.19 (brs, 1H), 7.74 (s, 1H), 7.11-7.27 (m, 7H), 6.74 (q, 1H, J=7.1 Hz), 3.91 (s, 2H), 2.11 (s, 3H). S-isomer: 19F NMR (d6-benzene; 6 eq of (R)-(+)-1-(1-naphthyl)ethylamine) d −77.76 (d, 3F, J=6.8 Hz, R-enantiomer), −77.74 (d, 3F, J=6.8 Hz, S-enantiomer).

Sources & evidence

ORD record
ord-14ab65b4732f44399cadd1cfabf6cbc6
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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