(+)-1-(1-Naphthyl)ethylamine → HCID 58934799, compound

HRID 855082Notes

Reaction equation

HRID 855082 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 58934799HCID 58934799, compound

Procedure

A racemic mixture of the compound prepared in Example 9a, Step 5 was resolved by chiral separation using Chiralpak AD-spring column eluting with iPA/heptane/TFA=5/95/0.1 and detecting at 254 nm to give a S-enantiomer as peak 2 with retention time 7.83 min. ESHRMS m/z 333.0519 (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).

Workup

  1. customwas resolved by chiral separation
  2. washeluting with iPA/heptane/TFA=5/95/0.1
  3. customto give a S-enantiomer as peak 2 with retention time 7.83 min

Sources & evidence

ORD record
ord-e77d332ab4f64e049a49d5c1ed833f4b
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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