Cyclohexane → HCID 49805573, compound

HRID 2367170Notes

Reaction equation

HRID 2367170 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C@H:17]3[C@@H:24]4[C@@H:20]([CH2:21][NH:22][CH2:23]4)[CH2:19][CH2:18]3)[CH:11]=2)=[CH:6][CH:5]=1)[CH3:2].C(N(CC)C(C)C)(C)C.[C:34](=O)([O:42]C1C=CC([N+]([O-])=O)=CC=1)[O:35][CH2:36][C:37]1[N:38]=[CH:39][S:40][CH:41]=1.C1CCCCC1>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C@H:17]3[C@@H:24]4[C@@H:20]([CH2:21][N:22]([C:34]([O:35][CH2:36][C:37]5[N:38]=[CH:39][S:40][CH:41]=5)=[O:42])[CH2:23]4)[CH2:19][CH2:18]3)[CH:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 81531DiisopropylethylamineHCID 18939632HCID 18939632, compoundHCID 67280381HCID 67280381, compound

Product 1

HCID 49805573HCID 49805573, compoundYield 63%

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 0.053 g (0.19 mmol) of (3aR,4R,6aS)-4-[(4′-ethoxybiphenyl-3-yl)oxy]octahydrocyclopenta[c]pyrrole, obtained in step 14.3., 0.04 mL (0.23 mmol) of N,N-diisopropylethylamine and 0.068 g (0.21 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 a 90/10 mixture of cyclohexane and ethyl acetate, 0.055 g (63%) of expected product is obtained in the form of an oil.

Workup

  1. customobtained in step 14.3

Sources & evidence

ORD record
ord-e187c911022344409b05efe7559920b0
Source dataset
uspto-grants-2014_04
Patent number
US08697883B2

Reaction notes

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