HCID 178445722, compound → HCID 178445746, compound

HRID 1036500Notes

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.[Br:38][C:39]1[C:48]([O:49][C@H:50]2[CH2:55][CH2:54][C@H:53]([C:56]([CH3:59])([CH3:58])[CH3:57])[CH2:52][CH2:51]2)=[CH:47][CH:46]=[C:45]2[C:40]=1[CH:41]=[CH:42][C:43]([C@:60]1([CH3:66])[CH2:64][O:63]C(=O)[NH:61]1)=[CH:44]2>>[NH2:61][C@@:60]([C:43]1[CH:42]=[CH:41][C:40]2[C:45](=[CH:46][CH:47]=[C:48]([O:49][C@H:50]3[CH2:51][CH2:52][C@H:53]([C:56]([CH3:59])([CH3:58])[CH3:57])[CH2:54][CH2:55]3)[C:39]=2[Br:38])[CH:44]=1)([CH3:66])[CH2:64][OH:63]

Participants

Reactant 2

HCID 178445722HCID 178445722, compound

HCID 178445751HCID 178445751, compound

Product 1

HCID 178445746HCID 178445746, compoundYield 31%

Procedure

(R)-2-amino-2-(5-bromo-6-(trans-4-tert-butylcyclohexyloxy)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 31% yield using (R)-4-(5-bromo-6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one as starting material. MS: m/z=419.29 [M−NH2]+. 1H NMR (MeOD) δ: 8.29 (d, J=9.0 Hz, 1H), 7.92-7.96 (m, 2H), 7.69 (dd, J=9.0, 2.0 Hz, 1H), 7.50 (d, J=9.3 Hz, 1H), 4.37-4.47 (m, 1H), 3.96 (d, J=11.5 Hz, 1H), 3.85 (d, J=11.5 Hz, 1H), 2.20-2.29 (m, 2H), 1.90-1.97 (m, 2H), 1.78-1.83 (m, 3H), 1.50-1.63 (m, 2H), 1.10-1.30 (m, 3H), 0.94 (s, 9H)

Sources & evidence

ORD record: ord-56bdbed9ee724a68b8885523bd0fbd73
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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