تفاعل #537017

ord-808e963c87c24968845c8312cdb0f12c

معادلة التفاعل

CC(C)OC(=O)N[C@@H]1Cc2[nH]c3ccc(C#N)cc3c2C1
((S)-7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-carbamic acid isopropyl ester
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
COc1ccccc1CCl
2-methoxybenzyl chloride
COc1ccccc1Cn1c2c(c3cc(C#N)ccc31)C[C@H](NC(=O)OC(C)C)C2
product
المردود 98.3%
COc1ccccc1Cn1c2c(c3cc(C#N)ccc31)C[C@H](NC(=O)OC(C)C)C2
[(S)-7-Cyano-4-(2-methoxy-benzyl)-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-carbamic acid isopropyl ester
المردود 98.3%

المذيبات

ظروف التفاعل

درجة الحرارة
50°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe reaction is cooled to room temperature
  2. 2
    أخرىThe white solid is collected
  3. 3
    غسيلwashed with water
  4. 4
    أخرىThe solid is dried in a 40° C. vacuum oven
  5. 5
    أخرىAfter drying

الإجراء التجريبي

A mixture of ((S)-7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-carbamic acid isopropyl ester (2.0 g, 7.06 mmol) and cesium carbonate (3.22 g, 9.88 mmol) in DMF (40 mL) is treated with 2-methoxybenzyl chloride (1.16 g, 7.41 mmol). The reaction is heated at 50° C. for 18 h. The reaction is cooled to room temperature and diluted with water (300 mL). The white solid is collected and washed with water. The solid is dried in a 40° C. vacuum oven. After drying, 2.80 g (98%) product is obtained as a white solid. LC-ES/MS m/z 404 [M+H]+, TR=2.83 min.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08486943B2uspto-grants-2013_07