Diisopropyl azodicarboxylate → (R)-2-amino-2-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)propan-1-ol

HRID 1036522Notes

Reaction equation

N[C@@](C1C=CC2C(=CC=C(O[C@H]3CC[C@@H](C(F)(F)F)CC3)C=2)C=1)(C)CO.[CH3:27][C@@:28]1([C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:44][CH:45]4[CH2:50][CH2:49][CH:48]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:47][CH2:46]4)[CH:40]=3)[CH:35]=2)[CH2:32][O:31]C(=O)[NH:29]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.CCOC(/N=N/C(OCC)=O)=O>>[NH2:29][C@@:28]([C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[C:39]([O:44][CH:45]3[CH2:46][CH2:47][CH:48]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:49][CH2:50]3)[CH:40]=2)[CH:35]=1)([CH3:27])[CH2:32][OH:31]

Participants

Reactant 4

HCID 5363146Diisopropyl azodicarboxylate

HCID 5462977Diethyl azodicarboxylate

HCID 67413569(R)-4-methyl-4-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one

HCID 178464725HCID 178464725, compound

Product 1

HCID 46196192(R)-2-amino-2-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)propan-1-olYield 35%

Procedure

(R)-2-Amino-2-[6-(4-pentyl-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 35% yield (and 21% recovered starting material) using (R)-4-Methyl-4-[6-(4-pentyl-cyclohexyloxy)-naphthalen-2-yl]-oxazolidin-2-one as starting material. Note that the starting material contained 20% impurity (mixture of reduced DIAD, reduced DEAD).

Sources & evidence

ORD record: ord-279f3ef3f79f4debb2877b905589f15c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

Loading…