HCID 178437275, compound → HCID 178437276, compound

HRID 1036482Notes

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:19][C@H:20]3[CH2:25][CH2:24][C@H:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]3)[C:12]=2[CH:16]2C[CH2:17]2)[CH:7]=1)([CH3:5])[CH2:3][OH:4].C([C@H]1CC[C@H](OC2C(C=C)=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:19][C@H:20]3[CH2:25][CH2:24][C@H:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]3)[C:12]=2[CH:16]=[CH2:17])[CH:7]=1)([CH3:5])[CH2:3][OH:4]

Participants

Reactant 2

HCID 178437275HCID 178437275, compound

HCID 178445747HCID 178445747, compound

Product 1

HCID 178437276HCID 178437276, compoundYield 76%

Procedure

(R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-vinylnaphthalen-2-yl)propan-1-ol was synthesized as per (R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-cyclopropylnaphthalen-2-yl)propan-1-ol (Example 215) in 76% yield using (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-vinylnaphthalen-2-yl)-4-methyloxazolidin-2-one as starting material. MS: m/z=365.48 [M−16]+. 1H NMR (MeOD) δ: 8.29 (d, J=9.0 Hz, 1H), 7.87 (d, J=2.0 Hz, 1H), 7.84 (d, J=9.3 Hz, 1H), 7.55 (dd, J=9.0, 2.3 Hz, 1H), 7.45 (d, J=9.0 Hz, 1H), 7.11 (dd, J=17.9, 11.7 Hz, 1H), 5.66-5.79 (m, 2H), 4.28-4.41 (m, 1H), 3.95 (d, J=11.5 Hz, 1H), 3.84 (d, J=11.5 Hz, 1H), 2.18-2.27 (m, 2H), 1.87-1.95 (m, 2H), 1.80 (s, 3H), 1.41-1.55 (m, 2H), 1.09-1.29 (m, 3H), 0.92 (s, 9H)

Sources & evidence

ORD record: ord-a57050f4eb5b4da9860bdf7c17f47a36
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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