Cyclohexane → HCID 49805572, compound

HRID 2367169Notes

Reaction equation

HRID 2367169 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C@@H:13]2[C@@H:20]3[C@@H:16]([CH2:17][NH:18][CH2:19]3)[CH2:15][CH2:14]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:30](=O)([O:38]C1C=CC([N+]([O-])=O)=CC=1)[O:31][CH2:32][C:33]1[N:34]=[CH:35][S:36][CH:37]=1.C1CCCCC1>C(OCC)(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C@@H:13]2[C@@H:20]3[C@@H:16]([CH2:17][N:18]([C:30]([O:31][CH2:32][C:33]4[N:34]=[CH:35][S:36][CH:37]=4)=[O:38])[CH2:19]3)[CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 81531DiisopropylethylamineHCID 18939632HCID 18939632, compoundHCID 67280859HCID 67280859, compound

Product 1

HCID 49805572HCID 49805572, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The process is performed according to the procedure described in Example 1, step 1.3. Starting with 0.059 g (0.21 mmol) of (3aR,4S,6aS)-4-[(4-chloro-1-naphthyl)oxy]-octahydrocyclopenta[c]pyrrole, obtained in step 13.3., 0.04 mL (0.25 mmol) of N,N-diisopropylethylamine and 0.066 g (0.23 mmol) of thiazol-4-ylmethyl 4-nitrophenyl carbonate (WO 2008/013 834), and after chromatography on silica gel, eluting with a 95/5 and then 90/10 mixture of cyclohexane and ethyl acetate, 0.017 g (19%) of expected product is obtained in the form of an oil.

Workup

  1. customobtained in step 13.3

Sources & evidence

ORD record
ord-800821048c3943ddb2961b05620c2ea0
Source dataset
uspto-grants-2014_04
Patent number
US08697883B2

Reaction notes

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