HCID 178445735, compound → HCID 178445759, compound

HRID 2389159Notes

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: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[Cl:66])[CH:55]=1)([CH3:65])[CH2:63][OH:62]

Participants

Reactant 2

HCID 178445735HCID 178445735, compound

HCID 178445751HCID 178445751, compound

Product 1

HCID 178445759HCID 178445759, compoundYield 39%

Procedure

(R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-chloronaphthalen-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 39% yield using (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-chloronaphthalen-2-yl)-4-methyloxazolidin-2-one as starting material. MS: m/z: 373.28 [M-NH2]+. 1H NMR (MeOD) δ: 8.14 (d, J=9.0 Hz, 1H), 7.93 (d, J=1.8 Hz, 1H), 7.81 (d, J=8.8 Hz, 1H), 7.71 (dd, J=9.0, 2.0 Hz, 1H), 7.39 (d, J=9.0 Hz, 1H), 4.26-4.37 (m, 1H), 3.73 (d, J=11.0 Hz, 1H), 3.69 (d, J=11.0 Hz, 1H), 2.18-2.26 (m, 2H), 1.85-1.93 (m, 2H), 1.46-1.58 (m, 5H), 1.05-1.26 (m, 3H), 0.85-0.94 (m, 9H)

Sources & evidence

ORD record: ord-220c3c1b82a94777b82c128cf709b559
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269043B2

Reaction notes

Loading…