diff --git a/lib/tokenize.cpp b/lib/tokenize.cpp
index 17d092a05..3557ccd1d 100644
--- a/lib/tokenize.cpp
+++ b/lib/tokenize.cpp
@@ -1430,9 +1430,19 @@ void Tokenizer::simplifyTypedef()
                             tok2->insertToken("*");
                             tok2 = tok2->next();
                         } else {
-                            tok2->insertToken("(");
-                            tok2 = tok2->next();
-                            Token *tok3 = tok2;
+                            // This is the case of casting operator.
+                            // Name is not available, and () should not be
+                            // inserted
+                            bool castOperator = inOperator && Token::Match(tok2, "%type% (");
+
+                            Token *tok3;
+
+                            if (!castOperator) {
+                                tok2->insertToken("(");
+                                tok2 = tok2->next();
+
+                                tok3 = tok2;
+                            }
 
                             const Token *tok4 = namespaceStart;
 
@@ -1447,12 +1457,15 @@ void Tokenizer::simplifyTypedef()
                             tok2->insertToken("*");
                             tok2 = tok2->next();
 
-                            // skip over name
-                            tok2 = tok2->next();
+                            if (!castOperator) {
+                                // skip over name
+                                tok2 = tok2->next();
 
-                            tok2->insertToken(")");
-                            tok2 = tok2->next();
-                            Token::createMutualLinks(tok2, tok3);
+                                tok2->insertToken(")");
+                                tok2 = tok2->next();
+
+                                Token::createMutualLinks(tok2, tok3);
+                            }
                         }
                     } else if (typeOf) {
                         tok2 = copyTokens(tok2, argStart, argEnd);
diff --git a/test/testsimplifytypedef.cpp b/test/testsimplifytypedef.cpp
index 2e0778838..ddfb6661f 100644
--- a/test/testsimplifytypedef.cpp
+++ b/test/testsimplifytypedef.cpp
@@ -151,6 +151,7 @@ private:
         TEST_CASE(simplifyTypedef115); // ticket #6998
         TEST_CASE(simplifyTypedef116); // ticket #5624
         TEST_CASE(simplifyTypedef117); // ticket #6507
+        TEST_CASE(simplifyTypedef118); // ticket #5749
 
         TEST_CASE(simplifyTypedefFunction1);
         TEST_CASE(simplifyTypedefFunction2); // ticket #1685
@@ -2354,6 +2355,22 @@ private:
         ASSERT_EQUALS("", errout.str());
     }
 
+    void simplifyTypedef118() { // #5749
+        const char code[] = "struct ClassyClass {\n"
+                "int id;\n"
+                "typedef int (ClassyClass::*funky_type);\n"
+                "operator funky_type() {\n"
+                "return &ClassyClass::id;\n"
+                "}}";
+        const char expected[] = "struct ClassyClass { "
+                "int id ; "
+                "operatorintClassyClass::* ( ) { "
+                "return & ClassyClass :: id ; "
+                "} }";
+        ASSERT_EQUALS(expected, tok(code, false));
+        ASSERT_EQUALS("", errout.str());
+    }
+
     void simplifyTypedefFunction1() {
         {
             const char code[] = "typedef void (*my_func)();\n"