HCID 178445751, compound → HCID 178466109, compound

HRID 1036490Notes

Reaction equation

N[C@@](C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2C2C=CC(OC(F)(F)F)=CC=2)C=1)(C)CO.[C:38]([C@H:42]1[CH2:47][CH2:46][C@H:45]([O:48][C:49]2[C:50]([C:66]3[CH:71]=[CH:70][C:69]([O:72][CH2:73][CH3:74])=[CH:68][CH:67]=3)=[C:51]3[C:56](=[CH:57][CH:58]=2)[CH:55]=[C:54]([C@:59]2([CH3:65])[CH2:63][O:62]C(=O)[NH:60]2)[CH:53]=[CH:52]3)[CH2:44][CH2:43]1)([CH3:41])([CH3:40])[CH3:39]>>[NH2:60][C@@:59]([C:54]1[CH:53]=[CH:52][C:51]2[C:56](=[CH:57][CH:58]=[C:49]([O:48][C@H:45]3[CH2:46][CH2:47][C@H:42]([C:38]([CH3:39])([CH3:41])[CH3:40])[CH2:43][CH2:44]3)[C:50]=2[C:66]2[CH:71]=[CH:70][C:69]([O:72][CH2:73][CH3:74])=[CH:68][CH:67]=2)[CH:55]=1)([CH3:65])[CH2:63][OH:62]

Participants

Reactant 2

HCID 178445751HCID 178445751, compound

HCID 178466108HCID 178466108, compound

Product 1

HCID 178466109HCID 178466109, compoundYield 35%

Procedure

(R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-(4-ethoxyphenyl)naphthalen-2-yl)propan-1-ol was synthesized as per (R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-(4-(trifluoromethoxy)phenyl)naphthalen-2-yl)propan-1-ol (Example 221) in 35% yield using (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-(4-ethoxyphenyl)naphthalen-2-yl)-4-methyloxazolidin-2-one as starting material. MS; m/z=459.45 [M−16]+. 1H NMR (MeOD) δ: 7.91-7.95 (m, 1H), 7.83-7.88 (m, 1H), 7.53 (d, J=9.0 Hz, 1H), 7.44-7.49 (m, 1H), 7.37 (s, 1H), 7.19-7.26 (m, 2H), 7.01-7.07 (m, 2H), 4.10-4.19 (m, 2H), 3.98-4.07 (m, 1H), 3.73 (d, J=10.8 Hz, 1H), 3.69 (d, J=11.0 Hz, 1H), 1.97-2.04 (m, 2H), 1.75-1.82 (m, 2H), 1.52 (s, 3H), 1.48 (t, J=6.9 Hz, 3H), 1.14-1.23 (m, 2H), 0.96-1.12 (m, 3H), 0.87 (s, 9H)

Sources & evidence

ORD record: ord-c40b27e0b6be42f5a516b33217e60c7c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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