Cesium carbonate → [7-(2-Benzyloxycarbonylamino-ethyl)-1-(3-chloro-benzyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid ethyl ester

HRID 2177126

Reaction equation

HRID 2177126 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][B-](F)(F)F)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[C:31]1[CH:40]=[CH:39][C:38]2[CH2:37][CH2:36][CH:35]([NH:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:34]([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[CH:49]=3)[C:33]=2[CH:32]=1)(=O)=O>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:45]([O:44][C:42](=[O:43])[NH:41][CH:35]1[CH2:36][CH2:37][C:38]2[C:33](=[CH:32][C:31]([CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[CH:40][CH:39]=2)[CH:34]1[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[CH:49]=1)[CH3:46]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 49761741Potassium benzyl N-[2-(trifluoroboranuidyl)ethyl]carbamateHCID 574767238-(3-Chlorobenzyl)-7-(ethoxycarbonylamino)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 57476722[7-(2-Benzyloxycarbonylamino-ethyl)-1-(3-chloro-benzyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid ethyl esterYield 75.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 22272177Toluene waterSolvent

Procedure

A mixture of potassium (2-(benzyloxycarbonylamino)ethyl)trifluoroborate (1,130 g, 3.96 mmol), cesium carbonate (2.58 g, 7.93 mmol), 8-(3-chlorobenzyl)-7-(ethoxycarbonylamino)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (1.3 g, 2.64 mmol), Pd(OAc)2 (0.030 g, 0.132 mmol) and 2-dicyclohexyphosphino-2′,6′-di-1-propoxy-1,1′-biphenyl (0.130 g, 0.264 mmol) under N2 in toluene/water 3:1 (15 ml) was heated to refluxed for 13 h. The reaction was filtered, the solvent evaporated and the residue purified by chromatography to afford 1.04 g of product as colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureto refluxed for 13 h
  3. filtrationThe reaction was filtered
  4. customthe solvent evaporated
  5. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-9f7119622a304926acf87d150dfec4bb
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Linked notes

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