HCID 178421576, compound → HCID 178464726, compound

HRID 2389176Notes

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:16][C@H:17]3[CH2:22][CH2:21][C@@H:20]([C:23]([F:26])([F:25])[F:24])[CH2:19][CH2:18]3)[CH:12]=2)[CH:7]=1)([CH3:5])[CH2:3][OH:4].C[C@@]1(C2C=CC3C(=CC=C(O[C@H]4CC[C@H](C(F)(F)F)CC4)C=3)C=2)COC(=O)N1>>[NH2:1][C@@:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][C@H:17]3[CH2:22][CH2:21][C@H:20]([C:23]([F:24])([F:25])[F:26])[CH2:19][CH2:18]3)[CH:12]=2)[CH:7]=1)([CH3:5])[CH2:3][OH:4]

Participants

Reactant 2

HCID 178421576HCID 178421576, compound

HCID 178464725HCID 178464725, compound

Product 1

HCID 178464726HCID 178464726, compoundYield 83%

Procedure

(R)-2-Amino-2-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-propan-1-ol was synthesized as per (R)-2-amino-2-[6-(cis-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-propan-1-ol (Example 259) in 83% yield using (R)-4-Methyl-4-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-oxazolidin-2-one as the starting material. MS: m/z=351.20 [M-NH2]+. 1H NMR (400 MHz, METHANOL-d4) δ ppm: 7.86 (d, J=2.0 Hz, 1H), 7.73-7.80 (m, 2H), 7.57 (dd, J=8.8, 2.0 Hz, 1H), 7.26 (d, J=2.5 Hz, 1H), 7.12 (dd, J=8.9, 2.4 Hz, 1H), 4.39-4.49 (m, 1H), 3.74 (d, J=11.0 Hz, 1H), 3.67-3.72 (m, 1H), 2.29-2.38 (m, 2H), 2.19-2.30 (m, 1H), 2.03-2.11 (m, 2H), 1.46-1.66 (m, 7H).

Sources & evidence

ORD record: ord-70bb78fdec8e48c2b8d5d20f38a329ca
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269043B2

Reaction notes

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