HCID 178445751, compound → HCID 178445810, compound

HRID 2389162Notes

Reaction equation

HRID 2389162 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]([Cl:68])=[C:51]3[C:56](=[C:57]([Cl:60])[C:58]=2[Cl:59])[CH:55]=[C:54]([C@:61]2([CH3:67])[CH2:65][O:64]C(=O)[NH:62]2)[CH:53]=[CH:52]3)[CH2:44][CH2:43]1)([CH3:41])([CH3:40])[CH3:39]>>[NH2:62][C@@:61]([C:54]1[CH:53]=[CH:52][C:51]2[C:56](=[C:57]([Cl:60])[C:58]([Cl:59])=[C:49]([O:48][C@H:45]3[CH2:46][CH2:47][C@H:42]([C:38]([CH3:40])([CH3:39])[CH3:41])[CH2:43][CH2:44]3)[C:50]=2[Cl:68])[CH:55]=1)([CH3:67])[CH2:65][OH:64]

Participants

3

Reactant 2

HCID 178445751HCID 178445751, compoundHCID 178445809HCID 178445809, compound

Product 1

HCID 178445810HCID 178445810, compoundYield 37%

Procedure

(R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5,7,8-trichloronaphthalen-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 37% yield using (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5,7,8-trichloronaphthalen-2-yl)-4-methyloxazolidin-2-one as starting material. MS: m/z=441.25 [M-NH2]+. 1H NMR (MeOD) δ: 8.42 (d, J=1.5 Hz, 1H), 8.28 (d, J=9.5 Hz, 1H), 7.89 (dd, J=9.0, 2.0 Hz, 1H), 4.31-4.42 (m, 1H), 3.78 (d, J=11.0 Hz, 1H), 3.72 (d, J=11.0 Hz, 1H), 2.14-2.22 (m, 2H), 1.85-1.93 (m, 2H), 1.63-1.76 (m, 2H), 1.56 (s, 3H), 1.04-1.15 (m, 3H), 0.90 (s, 9H)

Sources & evidence

ORD record
ord-8691a798b07c4ba98b65b66515a85562
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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