HCID 178445736, compound → HCID 178445760, compound

HRID 1036504Notes

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]([F:66])=[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[CH2:44][CH2:43][C@H:42]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:47][CH2:46]3)[C:50]=2[F:66])[CH:55]=1)([CH3:65])[CH2:63][OH:62]

Participants

Reactant 2

HCID 178445736HCID 178445736, compound

HCID 178445751HCID 178445751, compound

Product 1

HCID 178445760HCID 178445760, compoundYield 34%

Procedure

(R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-fluoronaphthalen-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 34% yield using (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-fluoronaphthalen-2-yl)-4-methyloxazolidin-2-one as starting material. MS: m/z=357.34 [M−16]+. 1H NMR (MeOD) δ: 8.25 (d, J=9.0 Hz, 1H), 7.92 (d, J=2.0 Hz, 1H), 7.88 (d, J=9.0 Hz, 1H), 7.68 (dd, J=9.3, 2.3 Hz, 1H), 7.49 (d, J=9.3 Hz, 1H), 4.33-4.42 (m, 1H), 3.94 (d, J=11.5 Hz, 1H), 3.84 (d, J=11.5 Hz, 1H), 2.17-2.26 (m, 2H), 1.86-1.95 (m, 2H), 1.79 (s, 3H), 1.46-1.58 (m, 2H), 1.08-1.27 (m, 3H), 0.90 (s, 9H)

Sources & evidence

ORD record: ord-033e674b3c2f43f5a7ea28a59502d66d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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