HCID 178421567, compound → HCID 178464712, compound

HRID 2389178Notes

Reaction equation

N[C@@](C1C=CC2C(=CC=C(O[C@H]3CC[C@@H](C(F)(F)F)CC3)C=2)C=1)(C)CO.[CH3:27][C@@:28]1([C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:48][C@H:49]4[CH2:54][CH2:53][C@H:52]([C:55]([F:58])([F:57])[F:56])[CH2:51][CH2:50]4)[C:40]=3[C:44]([F:47])([F:46])[F:45])[CH:35]=2)[CH2:32][O:31]C(=O)[NH:29]1>>[NH2:29][C@@:28]([C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[C:39]([O:48][C@H:49]3[CH2:54][CH2:53][C@H:52]([C:55]([F:56])([F:57])[F:58])[CH2:51][CH2:50]3)[C:40]=2[C:44]([F:46])([F:47])[F:45])[CH:35]=1)([CH3:27])[CH2:32][OH:31]

Participants

Reactant 2

HCID 178421567HCID 178421567, compound

HCID 178464725HCID 178464725, compound

Product 1

HCID 178464712HCID 178464712, compoundYield 75%

Procedure

(R)-2-Amino-2-[5-trifluoromethyl-6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-propan-1-ol was synthesized as per (R)-2-Amino-2-[6-(cis-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-propan-1-ol (Example 259) in 75% yield, using (R)-4-Methyl-4-[5-trifluoromethyl-6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-oxazolidin-2-one as starting material. MS: m/z=458.20 [M+Na]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.15 (dd, J=9.4, 1.6 Hz, 1H), 8.09 (d, J=9.3 Hz, 1H), 7.98 (d, J=2.0 Hz, 1H), 7.73 (dd, J=9.3, 2.3 Hz, 1H), 7.52 (d, J=9.0 Hz, 1H), 4.48-4.61 (m, 1H), 3.75 (d, J=11.0 Hz, 1H), 3.67-3.73 (m, 1H), 2.16-2.34 (m, 3H), 2.01-2.13 (m, 2H), 1.45-1.71 (m, 7H).

Sources & evidence

ORD record: ord-cd9e363c57494b55b7c4c24cf5b9d67b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269043B2

Reaction notes

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