HCID 178445724, compound → HCID 178445748, compound

HRID 1036492Notes

Reaction equation

[NH2:1][C@@:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:27][C@H:28]3[CH2:33][CH2:32][C@H:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:30][CH2:29]3)[C:12]=2[C:16]2[CH:21]=[CH:20][C:19](OC(F)(F)F)=[CH:18][CH:17]=2)[CH:7]=1)([CH3:5])[CH2:3][OH:4].C([C@H]1CC[C@H](OC2C(C3C=CC=CC=3)=C3C(=CC=2)C=C([C@]2(C)COC(=O)N2)C=C3)CC1)(C)(C)C>>[NH2:1][C@@:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:27][C@H:28]3[CH2:29][CH2:30][C@H:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:32][CH2:33]3)[C:12]=2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=1)([CH3:5])[CH2:3][OH:4]

Participants

Reactant 2

HCID 178445724HCID 178445724, compound

HCID 178445751HCID 178445751, compound

Product 1

HCID 178445748HCID 178445748, compoundYield 88%

Procedure

(R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-phenylnaphthalen-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 88% yield using (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-phenylnaphthalen-2-yl)-4-methyloxazolidin-2-one as starting material. MS: m/z=415.44 [M−NH2]+. 1H NMR (MeOD) δ: 7.93 (s, 1H), 7.88 (d, J=9.0 Hz, 1H), 7.44-7.52 (m, 4H), 7.38-7.44 (m, 2H), 7.29-7.34 (m, 2H), 4.00-4.09 (m, 1H), 3.66-3.75 (m, 2H), 1.97-2.04 (m, 2H), 1.75-1.82 (m, 2H), 1.52 (s, 3H), 0.92-1.23 (m, 5H), 0.86 (s, 9H)

Sources & evidence

ORD record: ord-3dc7570a770e4267866cbd411cb29aec
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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